Advice – My girlfriend gets aroused when stressed.

July 29, 2021July 28, 2021 / teatimewithtomato / Leave a comment

To sum it up, stress makes my girlfriend horny. This could be work stress, family stress, or studying for finals. Now usually I don’t mind this at all, right? We’ve been together about 2 years.

Well, we’ve hit some bumps in our relationship lately and we’ve been having some pivotal conversations about where the relationship is headed, what we’re realistically going to be, what we want in the short and long term. It’s not like we’re breaking up, but it’s a possibility; and it has made both of us feel pressure and stress as we work through it.

The issue with the stress is that it makes her want to get it on really frequently. I mean, REALLY frequently. Four or five times a day, and usually she wants to have sex right after a tense conversation. But, I’m the exact opposite of her. Stress kills my libido, and after a hard conversation I don’t mind laying down with her but literally the last thing on my mind is having sex.

This difference is creating a new level of issues during the hard time we’ve hit because she feels like I’m pulling away or don’t find her attractive or like I actually want to end things, despite the whole conversation we just had where I said I wanted to be with her. I’ve tried to explain that the stress is shutting me off, and she says she understands, but it’s clear she is still feeling hurt about it.

Any advice on what we, or I, should do?
Anonymous, Reddit.

Dear Anonymous,

Think of your sexual “drive” as composed of two different parts – an accelerator and a brake. Some people have really sensitive sexual accelerators – Sexual Excitation System (SES) – while others have insensitive accelerators that require a lot more to be activated. In short, the accelerator is reflective how fast you get turned on by your turn ons. An example of someone with a really sensitive accelerator is a person who gets aroused very easily with minimal input. Sexual accelerator operates under a completely independent spectrum than a sexual brake – Sexual Inhibition System (SIS). In short, the brake is reflective of how fast you get turned off by your turn offs. So an example with someone with a really insensitive brake is a person who doesn’t get turned off by something that might turn others off.

Our goal here is to “turn off the offs” and “turn on the ons”. We do that by identifying what our ons and offs are, communicating the essential expectations, and then managing the contexts around our ons and offs.

So first let’s parse your situation into to different parts: one for you and another for your girlfriend. This will help us identify what are your and your girlfriend’s turn ons and offs. After we discuss each of your perspectives, then we will talk about what you can both do to have a more fulfilling sex life together by adjusting the context around your ons and offs.

Let’s first talk about your headspace around arousal.

According to the dual control model, arousal is really two processes: activating the accelerator and deactivating the brakes … [I]t’s also a product of how sensitive your brakes and accelerators are to that stimulation.
Dr. Emily Nagoski, Come As You Are.

Based on what you have shared, it sounds like stress – particularly relationship stress – presses on your sexual brakes. That is a very common response to stress. Even if the actual status of your relationship is not in jeopardy, the sense of attachment in your relationship certainly could be. So when your brakes get inevitably hit, your body needs more time to acknowledge that this is still a safe connection that you can be erotically vulnerable with through intimacy. That does not happen on its own. You need time to heal and recuperate before you can turn off the offs – the relationship conflict points.

You said that your girlfriend’s behavior hasn’t been a problem for you in the past. I wonder if that is because the conflict itself didn’t pertain to you or if it was because the NRE overshadowed the brakes that were already being pressed. Has this been an issue in your previous relationships where you felt turned off immediately following a heated discussion with your partners?

This problem gets further exacerbated when your girlfriend keeps initiating sex even though you are not yet aroused. For you, this means that your sexual brake remains pressed, as a new iteration of the ongoing relationship stress. That is a problem. And one that perpetuates the existing set of issues.

So what does this mean for you?

You need a basis and a foundation of trust and safety in order to be aroused. Being rushed or pressured is not going to work for you because it is going to add to the stress that you already feel about your relationship. Even if the stressors are justified, well-intentioned, and on their way to resolution, there needs to be more of a space between the stress-inducing experience (like heavy discussions about the state of your relationship) and the erotic reconnection.

Now let’s talk about your girlfriend’s headspace around arousal.

Physiologically, anger and arousal have a lot in common. Psychologically, too. In your case, I think the anger emboldens you. It relieves you of compliance, and leaves you feeling more entitled. Anger highlights separateness and is a counterpoint to dependence; this is why it can so powerfully stoke desire. It gives you the distance you need. As a habit it can be problematic, but there’s no denying that it’s a powerful stimulant.
Esther Perel, Mating in Captivity.

I have two theories on what your girlfriend’s erotic headspace is like. And they’re not mutually exclusive.

The first possibility is that she has a very insensitive brake that allows for her to overlook the relationship conflicts in her arousal. In this possibility, her state of arousal is unaffected (or less than affected) by the stressors surrounding her personal life. This might be the case with your girlfriend if her normal libido maintains through times of conflicts as well as times of happiness.

The other and more likely possibility is that she has a very sensitive accelerator that allows her to get aroused with ease with her innately spontaneous sexual desire. In this possibility, her arousal is an outward manifestation of her stress mitigation effort. This arousal can come from a couple different places. Maybe she is able to switch gears really fast and easily tap into her fountain of spontaneous desire for sex with you. Maybe her arousability is a reflection of self-value affirming practice. Maybe her sense of stress is the heavy foot on that rests on her accelerator.

And the issue is not with any of those rationale. Her sexuality and desire is just as valid as your sexuality and desire. The issue is in how that conflict is resolved (or not resolved).

We also have additional data points to consider. When you communicate your current disinterest in sex, it sounds like her responses to this rejection is also layered. Whether she fears her own attraction or the stability in her relationship with you, the meta-feelings that she has about the rejection also shines a light on what she feels the most insecure about. Even though the rejection had nothing to do with her, her internal narrative around rejection unfortunately rewrites your stated intentions and desire for her. That is not only painful for her to feel through, but also difficult for you to overwrite her internal rewriting. And this in turn brings your caretaking to the forefront, which is also not conducive to an erotic mindframe for you. For her, her reaction might come from a complicated but powerful concoction of her sexual upbringing, self-criticism, and relationship doubt. Her feelings are just as valid and real as yours.

Now that we’ve touched on each of your perspectives, let’s do a deeper dive on how to bring both of you together.

When we feel distressed, our attachment object is our safe haven. Even – or perhaps especially – if our attachment object is the source of our distress.
Dr. Emily Nagoski, Come As You Are.

So far, we’ve covered that your erotic headspace and your arousal cues might be very different from your girlfriend’s erotic headspace and her arousal cues. That is normal. You two have led completely different lives before you met each other. Also, you each contend with completely different social conditioning around your gender and sexuality. Our goal here isn’t to bring the other completely over to one side. Instead, we should aim to understand where you are each standing, find out what makes each of you feel safe & supported, and settle on a happy medium where neither of you are dealing with a crisis of faith in your relationship.

For you, your goal is to turn off your turn offs. I think it would be beneficial to communicate your headspace and the meta-feelings around your relationship conflict points. This will create space for her to also relate with you about her own headspace and her meta-feelings about the recent stressors. Then reflect on what you need to feel safe to engage in intimacy with your partner. That can look like a soft verbal reaffirmation that she is just. as committed to work through this with you. It can also look like a long, intimate cuddle to start physically reconnecting before sex even comes into play. Or it might look like her giving you five minutes on your own to process your feelings and meta-feelings about the heavy discussion you two just had. Whatever it is, be courageous and reassure her that you are not abandoning her and that you also want to keep working on this relationship with her.

For her, she’ll also need to come up with a way to interrupt her negative feedback cycle upon rejection. The knives that she wields are sharp and context-dependent. If she has to leave you alone for sometime while you recuperate, it’s going to feel exactly like the wrong thing to do. That just isn’t how her attachment muscle is set up. But consistently doing so even if for five minutes will allow her to build trust that you will keep coming back, that you are going to keep choosing her. And that five minute break will help you switch your mental gears and get back into your erotic headspace with the person you’ve been working so hard to maintain a relationship with.

For both of you, it might be mutually beneficial to look to what intimacy really means for both of you. Eroticism and intimacy goes far beyond just the act of penetrative intercourse. A skin-to-skin cuddle can be just as erotically charging as PIV in the right context.

Good luck!

Tea Time with Tomato is an informative relationship and sex advice column for both monogamous and polyamorous folks. By submitting your post, you agree to let me use your story in part or in full. You also agree to let me edit or elaborate for clarity.

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Advice – I want to try anal, but cannot relax. [NSFW]

February 23, 2021February 22, 2021 / teatimewithtomato / Leave a comment

I’ll start this off by saying, my fiance is an ass lover. He is OBSESSED with my ass. It’s not large by any means but during sex he always compliments it, loves doggy because he loves to see my ass, likes when I wear leggings so he can rip them open and fuck me behind, told me that he loves when I sit on his face , etc.

He has been wanting to do serious anal for a long time, he has mentioned it before a lot and I am not opposed to it, I would love to be able to enjoy anal and be able to please him that way, however I cannot relax enough during it for it to feel good.

I like when he puts his fingers in my ass while doing PIV and it always feels good when he does it with a finger, but all the times we have attempted with his dick it just doesn’t feel good, it is painful as hell and I can’t relax. I don’t know why or how to make this better. We use TONS of lube when we try so lube is not the problem. I would love to be able to do anal with him and fulfill one of his fantasies but I just can’t do it.

I am looking for good tips to try and ease the process. We have talked about getting a butt plug and having him use his fingers and work a plug in and do PIV to see if it helps ease my butt, though I’m not sure if that will actually help? I think his size and being an anal “virgin” intimidates me.

I would also like to mention that I also can’t get over the feeling that it makes me feel like I need to poop, even after using the restroom beforehand and cleaning out I always have the “I need to poo sensation” when he puts his dick in.

Please leave me any advice, tips, or tricks.
Terry, Reddit.

Dear Terry,

A very common mistake among anal newbies is that you can go straight from little to no stimulation to penetration. This is a particularly dangerous myth because your sphincter is just not ready for that type of action without the proper warmup. When it comes to proper anal intercourse warmup, there are three major components.

The first component is lubrication. Some folks don’t know that an anus don’t self-lubricate the same way a vagina does. It sounds like this part you’ve already got down. But I think it’s also very important to consider multiple different types of lubes. Sex With Emily goes into great depths about the differences between silicone-, water-, and oil-based lubes that I think you should take a look at. In short, silicone-based lubes like Uberlube are more suitable for longer plays while water-based lubes like Lube Life are easier to clean up. If you find that you keep having to reapply lube, you might benefit from switching to a silicone-based lubes.

The second component is training. Not many folks know this, but sphincter is a muscle! And like any other muscle, you are going to need to work it out and stretch it out to make sure that you can have penetrative intercourse. You’ve already mentioned anal plugs, and I think that would be a great idea. But I would also suggest anal training sets like this set from Babeland or this set from Adam & Eve to start training your interior and exterior sphincter for penetrative play. These flared-base anal trainer sets are especially great because they vary in size. Depending on your fiance’s penis size, you should absolutely practice. It is also very important to keep in mind that silicone is not at all like flesh of the penis. So what I’ve found helpful is to warm up the trainer plugs in warm water or – even better – a partner’s mouth before lubing it up for penetrative play.

I’ll also mention here that you should never use an anal toy that doesn’t have a flared base. You wouldn’t want to have an awkward trip to the emergency room because you lost your plug in your butt, right?

The final and the most important component is play!

The more pressure you put on your anus to perform, the more difficult it is going to be to actually be in the mindset to have anal sex. If you find that anal sex is always in the context of PIV, it might be beneficial to temporarily dock PIV so that you can enjoy anal play that doesn’t immediately involve genital penetration. You mentioned that you’ve enjoyed digital stimulation from your partner. So incorporating more of that into your sex life without his penis being in the equation at all should help you get more comfortable with anal play in general.

Just take it a bit slower.

I also want to touch on being an anal virgin. Our culture already has such a weird and warped standards around virginity as is. And often times, it is incorrectly associated with purity and sanctity. We don’t need to take those toxic beliefs forward in our relationships today. A lot of folks misunderstand that virginity is not a physical aspect you lose when you have penetrative intercourse with your reproductive organs. Instead, it might be more beneficial for you to reflect on your virginity as a spectrum, rather than a binary. You’ve already had your fiance’s finger in your ass. And in that specific way, you are no longer an anal virgin in the same way that having anal sex as a “God’s Loophole” doesn’t make you a virgin either.

As for the “needing to poop” sensation, that is also natural! It’s your body’s way to expel that which don’t naturally belong in your rectum, which in your case is your fiance. For your fiance, that generally translates to a gripping sensation that should provide an intense pleasure for him through his penis. For you, that “needing to poop” sensation is one directional – out of your ass. But practicing with the trainers and his fingers should definitely help with managing that reflex in the context of anal sex. Your brain just needs a little help rewiring the sensation from anal stimulation as something other than poop-oriented, that’s all.

Good luck!

Advice – I used to be a cam girl. Should I tell my boyfriend?

February 17, 2021February 16, 2021 / teatimewithtomato / Leave a comment

About four years ago, I [22F] was a web cam girl for a few months. It still haunts me to this day and I am very fearful of my now partner [28M] finding this out because I know that he will torture me over this. It is such a slim chance of him finding out but there are pictures and videos of me online that have been reposted on some websites and that makes me feel so sick to even think about. I love him so much and I am a great girlfriend to him but this makes me feel undeserving and shameful in a way. Should I tell him this or does it even matter much? I would rather die than have him know. I want to get them removed online but I just don’t know how. I feel like if I tell him this it will just define me and I don’t ever want him to see me differently.
Melody, Reddit.

Dear Melody,

There are so many different types of pain and misunderstanding packed in such a short post.

There is such a powerful, pervasive, negative cultural stigma around sex work. And it looks like you have internalized some of the shame (“… this makes me feel undeserving and shameful”), disgust (“… that makes me feel so sick to even think about”), and guilt (“I am very fearful of my now partner finding this out”). Each of those are interwoven into not just the way you conceptualize and experience your romantic relationship with your partner but also with yourself.

I want to spend some time with each of those feelings and what they could mean. Each of those feelings intersect with each of the relationships you have with your past self, your current self, and your boyfriend. Then we will talk about whether or not you should tell your boyfriend and how you should if you do decide to share this part of your past with your partner.

Let’s first focus on your relationship with yourself.

Through all of these internalized social stigma about sex work, it is very clear that there is a major disconnect around reconciliation between your past as a sex worker and your present reality as your partner’s girlfriend. And deeply imbedded in that disconnect is a self-inflicting wound that unfortunately acts as the mouthpiece for many of the negative feelings you are experiencing right now. And each time those negative feelings come up, they are immediately measured against the dysfunctions within your past self (shame), dysfunctions within your current self (disgust), and dysfunctions within your romantic relationship (guilt).

Shame is a fundamental reflection of external societal pressure making an impression on your past. In reality, sex work is work. People engage with sex work for multitude of different reasons. So camming might have been a means to support yourself financially. It could have been born out of self-empowerment exercise through which you explored previously unrealized parts of your sexuality. Ultimately, your rationale surrounding why you chose to pursue camming is unimportant. What is more important is recognize that it happened, reflect on what it meant to you as a person, and move forward with new experiences.

Disgust is a more nuanced feeling that has deeper roots around how you perceive your experience with sex work. Based on what you have shared, it is unclear if your sense of disgust is just a different manifestation of the same shame or if there are deeper roots in your general attitude about sex work. It might be more beneficial for you to do some digging by yourself or with a sex-positive therapist to heal and recover from your experience.

Out of the three, guilt is the easiest to explain. Some of your guilt originates from obscuration of your past from your partner. As in, you feel that you should have come clean about your sex work experience with your partner before you got into a romantic relationship. It could also be possible that your guilt stems from internalization of negative stigma around sex work. As in, you have difficult time moving beyond your sex work history. And because you have such struggle moving past it, your inability to move past it manifests in guilt.

Now let’s talk about your relationship with your boyfriend.

I was quite alarmed to read that you feel that your boyfriend would “torture” you if he found out about your history with sex work. I wondered if that could be a sign of a very dysfunctional relationship with your partner where your partner never reacts well to aspects about yourself and your past, even in your most vulnerable moments. I also wondered if that was another manifestation of the internalized social stigma around sex work on his behalf as well. Either way, your pre-emptive reaction to this hypothetical conversation with your boyfriend tells me two things.

First is that your relationship does not feel like a safe place to share this very vulnerable aspect about yourself. If his immediate reaction is to assume negative judgment about your previous work history, it says a lot more about how little foundational trust there is to support any of the vulnerability you want to share with any prospective partner, much less this one. We will talk more about this in the next section when we discuss if and how you should approach this discussion.

My second thought is that being a great girlfriend has nothing to do with your previous sexual or work history. Your experience with sex work was only for a few months several years back. And while that might be a pertinent information that your partner might want to be privy to, absence of that sharing does not predicate that you are a bad partner at all; it just makes you a hesitant one. And perhaps, for a good reason.

A good partner should enthusiastically embrace as many aspect of your personhood within reason. And if you feel that your boyfriend will shame you for your past, then that is unbecoming of him as a partner.

I think it would be worthwhile to consider why you might want to disclose your sex work history to your partner.

Since we have just established why you don’t feel that it is safe to talk about your camming experience, we will need a better way to determine what you need in order to feel safe to share.

Perhaps a good start to that discussion is by first gauging how his real-life reaction might be like by bringing up a similar experience someone else might have had. This accomplishes two goals. First is that it takes the burden off of you since you’d be talking about someone else’s experience. But more importantly, this helps you gather more data on how he might react if this did apply to you. This would provide valuable data for your current relationship predicament.

Another valuable exercise that you can implement today is to shadowbox and project what that safe space might even look like. Imagine in your head what context you need in order for you to feel safe talking about your sex work history. What level of trust do you feel that you need to preemptively establish with your partner? Does this take place in a one-on-one setting or with other loved one in attendance? Better fleshing out what that type of dialogue might look like should help you do the necessarily emotional labor associated with the actual dialogue itself.

You should only have to share that which you feel comfortable sharing. And if you don’t feel comfortable sharing your history (and you aren’t even sure how to get to that level of comfort), you should know that your boyfriend is absolutely not at all entitled to know every aspect of your sexual or professional experience.

I also want to touch on possibility of videos and pictures that might be posted on internet without your permission.

I strongly urge you to contact organizations like March Against Revenge Porn, Without My Consent, and Cyber Civil Rights Initiative (CCRI) to help take down those videos from websites who published your contents without your explicit consent. Doing so will greatly alleviate the anxiety you feel about not just your boyfriend but all the people who are non-consensually engaging with unethical sexual material online.

You are not alone.

Good luck.

Advice – I just tested positive for chlamydia. Did my boyfriend cheat?

February 11, 2021February 10, 2021 / teatimewithtomato / Leave a comment

On December 16th, I got an STD test where I tested negative for chlamydia and gonorrhea. At that point, I had been in a monogamous relationship with my boyfriend since end of October. In September, he had his last STD test in which he tested negative for everything and he claims that he wasn’t with another girl between then and when we met. Anyways, I just now had another test after some symptoms and I tested positive for chlamydia. So my question is, is a result of infidelity? Is it possible that I got it before I met him and it didn’t show up in my results in December for some reason? Or that he has had it all this time and simply lied to me about getting tested, and I just now contracted it from him?
To add more background, we don’t use protection and have never used protection. I’m on birth control and trusted that he had gotten tested, and although we were both aware of the risks of pregnancy we choose to be stupid because we both enjoy it so much more without a condom.
Essentially, before I accuse him of lying or cheating I would like to know what all the possible solutions are. Thank you in advance.
Felicia, Reddit.

Dear Felicia,

Let us first establish the timeline.

September: Your boyfriend gets tested negative for everything.
Between September & October: You two meet. He claims to not have slept with anyone in this timeframe.
End of October: You enter into an exclusive relationship with your boyfriend.
Mid December: You test negative for chlamydia and gonorrhea.
February: You test positive for chlamydia.

While CDC isn’t clear on the incubation period for chlamydia, this 2011 study indicates that the chlamydia can incubate between seven to twenty one days. If that is the case, then it is evident that you contracted chlamydia following your mid December test. If your boyfriend had contracted chlamydia prior to October, then you should have already started seeing signs of the infection about a month before the test. It just seems highly unlikely that he lied about his September STI screening and happened to have had asymptomatic chlamydia the entire five months you’ve been together.

With that said, it isn’t completely out of possibility that you somehow tested negative for chlamydia while carrying it back in December. But the likelihood of that seems highly improbable.

So in short, it does seem likely that he has cheated.

But this is really all just confetti.

Even if we establish that you contracted chlamydia through his sexual infidelity, we have a bigger issue with lack of proper safety precautions. While it is true that BC pills protect against unwanted pregnancy, it does nothing for unwanted STI transmission as you have discovered here. Furthermore, condoms do not protect against other skin-to-skin STIs like herpes or syphilis.

It is very important to keep in mind that there are multitudes of risk to be aware of. And while your chlamydia might do away with a single dose of azithromycin, the emotional harm that comes with contracting an STI has more profound implications. For one, it is apparent that your soon-to-be-ex-boyfriend also had very different risk thresholds as it pertains to COVID transmission. After all, we are all currently in the middle of a serious global pandemic. Even outside of the pandemic circumstances, most folks have put dating on hold until the overall risk levels becomes more manageable. And each risk you take is a successive undertaking that you need to be conscientious of for not just yourself but for all people you come in contact with.

Please be mindful of the risks you are taking for not just this relationship but for all other relationships you might have in the future.

Good luck!

Advice – How can I learn to heal after a breakup?

February 3, 2021February 2, 2021 / teatimewithtomato / Leave a comment

My boyfriend [29M] and I [27F] have decided to mutually split up after lockdown. We are very different people; he wants children and I don’t, for example. A lot of things in the short term have been the final nail in the coffin for me. We had a chat today and agreed that we will break up sooner rather than later. Do any of you have any tips in terms of getting over the love of your life who would be perfect if it wasn’t for one thing? Our relationship is great but then we can’t be together. How do you reconcile yourself with that? My brain hurts trying to figure it out.
Bebe, Reddit.

Dear Bebe,

I am so sorry to hear that you are in the middle of such a disorienting end to an otherwise good relationship.

Even quality relationships can end for countless different reasons. Some of them explode spectacularly over a discovery of a chance infidelity. Some of them collapse through many years of built-up and unresolved resentment. Some ends are completely irrational while others are calm transitions to something other than a romantic relationship.

And perhaps that is a potential mindset where we can first rest in, that this does not necessarily have to be a definitive end to your connection with your ex-boyfriend. Queer communities often comment on the importance of chosen family, or a group of people who are bound by choice and not necessarily by blood. For many of those chosen family members in queer communities, they happen to be former lovers or distant flings. And so, it could be possible that the end to your romantic connection with your ex-boyfriend can instead be reframed as a transition and a beginning to your platonic connection.

Another important point to make here is your perception and experience with grief and loss.

It sounds like both you and your ex-boyfriend understand logically and rationally that the breakup is necessary. But even if you and your ex-boyfriend logically agree and accept that the end is inevitable, it doesn’t necessarily mean that you and your ex-boyfriend have each come to terms with it emotionally.

And Bebe, I think it is possible that you feel a sense of regret, not for the great relationship you had with this incredibly human being, but how things could have been different if those things were different. It is very easy and also dangerous to trap yourself in that mental loop of different hypothetical scenarios. That trap is easy to fall into because it lives entirely in your own headspace, and therefore requires no change or growth from the people involved. That trap is dangerous because it really is a hypothetical disguising as reality. The trap itself is an emotional distress coping mechanism. But there are cleaner ways to recover and heal than through this mental loop.

It is important to keep in mind that this one thing isn’t just any One Thing. Along with openness of your relationship and clear emotional incompatibilities, disagreement on parenting has very little room for negotiation or change. So be kind, allow yourself to breathe through those hypotheticals, and break the loop if you can see the repeat patterns in your head.

And I want to come back to reframing this breakup as a transition to a new beginning.

If you feel it is necessary, many do take the time off to heal before reconnecting with their former paramours. And if it is true that everything else was perfect and this was just the one thing that didn’t work for your romantic relationship, then you can be there for each other after you’ve both healed and recovered from the pain of this breakup. And perhaps from the charred remains of your former love can rise a different but equally meaningful friendship.

I want to leave you off with a thought that the process to heal from breakup looks different for everyone. For me, I get comfy and watch my two breakup flicks: Eternal Sunshine of the Spotless Mind and Forgetting Sarah Marshall. Through those movies, I conscientiously chew on my pain through the similar pains the characters on the screen share. And it could be that your healing process can involve a reservation at a rage room (with proper safety precautions), long stomps at a local hiking trail, or multiple scream-cries into your squishiest Squishmallow.

In the meantime, make sure that you have space away from your ex-boyfriend so that each of you can heal.

I feel for your heart and I really hope that your healing process can be as fruitful as it is meaningful.

Good luck!

Advice – I have no idea how to date.

January 14, 2021January 13, 2021 / teatimewithtomato / Leave a comment

I was single for 4 years since I moved cities for a job after graduating college. Since my field is very competitive, and with not many women, I decided to put my dating life on hold and focus on my career.

I have no regrets as to that decision and I am now professionally established and doing quite well.

I have however been working from home since March for obvious reasons and suddenly I realised that I was lonely. I live with two close friends and while we spend a lot of time together, it felt like something was missing.

Like everyone at home, I decided to download a dating app and try my hand at it.

Enter Peter (26M). By all means, the perfect partner: we have similar interests, make the same dumb jokes, and he is both brilliant and attractive.

We have been dating for a little over 3 months now, my friends love him, I get along with his friends and it’s all going great except- I am not feeling it. He often talks about the future and my immediate reaction tends to be just freeze up, pipe up a platitude and smoothly change the topic.

When this first started, I thought I wanted something casual and in the now, and we were on the same page but I feel like that might have changed for him after seeing how well we click?

For me though, I still have trouble being vulnerable around him, and instead of excitement, I feel increasing amounts of dread before every date.

On Sunday evening, he confessed to loving me and I told him that while I wasn’t at love yet, I did like him and he said that was enough for him for now.

I know I should break up with him before it gets any more serious and I hurt him, but at the same time I am terrified: if I can’t love someone like him, am I going to find love outside of this relationship? Should I settle for this camaraderie?
Lily, Reddit.

Dear Lily,

I am a big fan of Brene Brown’s work.

I’ve referenced her work once or twice on this column. I often recommend her podcasts – Unlocking Us and Dare to Lead – to others who want to learn more about what she has to offer. At the end of each podcast episode, Brene Brown asks her guests a series of rapid-fire questions that start with this question.

“Fill in the blank: Vulnerability is ….”

Recently, she had President Obama who answered, without hesitation, “Inevitable. Be open to it.” And Lily, I think this advice would be remiss if I don’t echo the same sentiment to you.

Part of what makes dating so thrilling and scary at the same time is that becoming vulnerable is an essential part of dating. If dating was a book, vulnerability would be the very binding that holds all the pages together. It is through the vulnerabilities shared that we weave together and bind our histories in a relationship. For some, shared vulnerability can look like making impactful life decisions together. For others, it can look like being open and honest with each other about sensitive topics. And for your partner Peter, his acknowledgment of his deep adoration for you as a person could have been another vulnerable thread to weave into your history together.

And let’s talk more about that concept – a history together.

Each person in a relationship comes with our own respective personal histories – narratives that we each tell ourselves which define who we are as individuals. It could be as simple as characterizing yourself as a poor picker of fruits, enforced through series of bad experiences with spoilage. Or it can be as complex as repeat behavioral patterns found in our partners.

As I was reading through your initial post, I gathered that you are quite adept at acknowledging your own context and making quick decisions based on your desires. That ability is reflected in your decision to pursue your career. It is also in your decision to start dating three months ago. And your interpersonal assessment even extend to those around you – specifically in the ways you can assess how Peter fits into your life and how your friends feel about him. You have even had the clairvoyance to pick out your own avoidant patterns whenever Peter brings up what your relationship might look like in the future.

Then I wondered what type of stories that you might tell about yourself, beyond what you’ve already shared in this incredibly brief history of you. You say you initially wanted something more casual. But I am curious if that was in response to the absence you felt when you first started dating or if it was a learned one you adapted through your history with Peter.

So let’s go back and ask ourselves the same question that Brene Brown asked Obama: Vulnerability is _____.

There was a point in my life when my answer to that question would have been “terrifying.” I was gripped with the insecurity and anxiety about the folks I was dating. It made me rigid and held me tight until I could no longer bear the weight of the insecurities and anxieties. And so, I found myself going through relationships against a checklist of flags. I asked myself the same exact questions you did. I wondered that if I couldn’t make it work with this particular partner, I just couldn’t see how I could make it work with someone else.

At some point, I realized how that process made me feel and started investing more of myself into my relationships. That meant I had to make myself more available to not just sharing my own vulnerability with others but to respond when others shared their vulnerabilities with me. At that point, my answer to the question changed to “empowering.”

And Lily, that particular reflection has made all the difference in my relationships.

Ask yourself what factors contribute to your hesitance to be vulnerable around Peter. Perhaps you’ve had some bad past dating experiences that conditioned you to associate vulnerability as something to be avoided. It could also be a reflection of your male-dominated career where vulnerability is seen as a weakness. Or perhaps your experience with vulnerability has deeper roots in your childhood or adolescent experiences. Try to dig deeper and see why your perception of vulnerability is so intertwined with fear and avoidance.

Vulnerability is the main way we build our marbles of trust.

It does sort of become a catch-22 when you think about the feedback loop of trust building. You need to be vulnerable in order to build trust. But you can’t trust enough to be vulnerable. If we define trust as a basic building block of relationships, we need to be mindful in the way we build on trust through our relationship experiences and shared vulnerability.

Perhaps a good starting point is to openly discuss with Peter how you sometimes freeze up when the topic of your relationship’s future comes up. You can use this discussion to assess and accomplish three different goals.

First goal is to create a safe and secure space for yourself. For me personally, I have found that it is easiest for me to get comfortable when I am surrounded by softness – such as blankets, bare skin, and compassion – and the people I trust – such as lovers, close friends, and family. The contextual clues that allow you to be comfortable in your vulnerability might look different than mine. In your head, visualize a mental and physical space that brings you safety and comfort. And do your best to bring that vision into reality. Even if your first attempt isn’t perfect, it’ll get you closer in your next attempt.

Second goal is to set some expectations. You can do this by drawing a basic idea around how you think this conversation is going to go. Anxiety will likely have some say on perpetuating your internalized dread. But anxiety is not the only feeling that needs to have a say. Sometimes, it can be as simple as saying out loud “This conversation is going to make me feel very vulnerable”, either to yourself before the conversation or as a preface to the conversation with Peter.

The last and the most important goal is to measure the trust building. Spoken words have power. Stating out loud “This conversation made me feel closer to you” can feel a bit sentimental. But it is very meaningful to communicate how intense the conversation felt and make space for reflection & reciprocation as well.

Photo by Tea Creative │ Soo Chung on Unsplash

I will leave you off with this final thought.

There is a big misconception in modern dating. And it is that you should love and care for your partner to the exact same way that your partner loves and cares for you.

This perception is flawed because it incorrectly assumes equality. As we talked about, each of us come with our own respective histories that determine who we are as individuals. As such, we harness different characteristics and present our care and affection in unique ways.

This misconception is one of the reasons why there is such a heavy weight and burden around the words I Love You in the western culture, because a non-immediate reciprocation is considered a red flag.

The truth is that different people love in different ways. And to expect that you should care for Peter in the same exact way that Peter cares for you might be misguided and unfair. Instead of immediately jumping to a breakup, it might be more beneficial for you to first reflect on the quality of the relationship from your own perspective, isolated from how Peter perceives his relationship with you. Because even if this particular relationship doesn’t stand the test of time, this exercise will help with your next one.

Good luck!

Advice – My girlfriend’s best friend wants to watch us have sex [NSFW].

January 8, 2021January 7, 2021 / teatimewithtomato / Leave a comment

My girlfriend (“Izzy”) and her best friend (“Mel”) are obviously very close. They talk pretty much about everything. I’m pretty sure she has told her a lot about our sex life. Sometimes, we even talk about it occasionally when the three of us are together. I’d say we are all about the same sexually, in terms of our openness to trying new things and our kinkiness. Well, the other day, her friend mentioned something that turned her on that she hasn’t ever done before. She admitted to my girlfriend that she really wants to watch another couple have sex. They spoke more about it and went into the details of it.

My girlfriend asked her if she thought the idea of watching us have sex would turn her on. She agreed and said that’d be even better since she knows both of us. The friend clarified that she doesn’t want to join, but may would want to touch herself if we were okay with it. My girlfriend pretty much agreed on the spot to it all. Later, my girlfriend brought it up to me all excited. It sounded like she had already made up her mind for both of us. She was telling me when we were going to do this and how great it’d be. I had to stop her to tell her that I never agreed to it. She said “yeah but I knew you would.” She is honestly probably not wrong about that, but it still hasn’t given me much time to think about the logistics of it.

The plan was for it to happen this coming weekend. I wanted to see if anyone had any advice on this. I honestly think it could be hot. I just want to make sure there isn’t anything that I’m not understanding or thinking through about it. Because honestly it’s mostly my other head that’s doing the thinking right now lol. Has anyone else ever done this? How does it work? Is it enjoyable? What should I do?
Michael, Reddit.

Dear Michael,

What you are describing here is a bread-and-butter voyeur/exhibitionist kink scene. But even before we get to what it might actually look like or what you can do to make this an enjoyable experience, we need to talk about how this was all initiated.

Let’s first talk about your ambivalence. It is one thing to have open and frank conversations about sex and sexuality, but another to become part of it. I get the feeling that the conversations about sex and sexuality that you’ve had with Izzy and Mel are deeper and more practical than it appears on surface, especially so if you can gauge each other’s kinkiness through conversations. But like you, I don’t really get the sense that this is much about what you or Mel wants to do, but rather what Izzy wants you two to do.

Here is a good example of why this feels so icky. When you initially pushed back and said you never consented to this, her response was that she knew you would say “yes.” So in that one set of exchange, she not only disregarded your “not yet” but also inserted intent behind her presumed “yes.” Like you said, she had already made up her mind, with very little regard for your actual consent. Based on how Izzy has steamrolled your consent, consider that it is also very possible that Izzy could have steamrolled Mel’s consent here as well.

Remember, a lot of what happened beyond what you saw or heard and are only framed in Izzy’s recollection and retelling of her conversation with Mel. And because much of what we have here are she-said-she-said, it is also unclear if Mel actually initiated this conversation about watching you two have sex or if Izzy did.

Let’s now operate under the presumption that everything was on the up-and-up.

Preparation is absolutely important because there are two connections at risk from this going wrong: Izzy’s romantic relationship with you and Izzy’s best friendship with Mel. There is a lot at risk and committing to this weekend is far too early!

It might be beneficial for you to confirm with Mel on your own that this conversation happened as Izzy claims it did. This accomplishes two specific goals.

First goal is that it clarifies the questionable consent. Hearing it directly and clearly from the third party of interest is one of the reasons why Don’t Ask Don’t Tell policies in non-monogamous relationships are such a bad sign. This also allows you and Mel to develop your own connection. Voyeurism and exhibitionism operate under the assumption of safety and security above all. And it sounds like most of your conversations about sex with Mel has been attended to by Izzy as well. Even if the quick touch-base with Mel doesn’t immediately spark a sexual connection, allowing for a space for her to feel safe with you will also help her (and you) feel safe when she watches you and Izzy have sex.

Remember, proactive consent is sexy.

If you have confirmed that Mel is as into this as Izzy said she would be, great! Now is a great time for you three to get together and each weigh in on how you each think this is going to go. Even if it is a dry mechanic-oriented conversation (“We are going to take clothes off. Then you sit down in the chair some distance away where you can masturbate while watching us.”), this conversation can be used to elevate the sexual tension. This also has the added benefit of no unexpected Big surprises on the next evening that Mel comes over, since ya’ll would have already talked it out.

Another important conversation you three need to have is a safe word. Since Mel won’t be physically engaging in this kink scene with you, determining and agreeing to a safe word will allow anyone to halt the scene if necessary.

Another aspect of this to consider is that there is going to be a lot of new elements for you as well. You aren’t just having sex. You will be having sex in front of someone new, which is already complicated enough without having to consider that that same person will also be masturbating to you. You might get in your own head about whether or not you are hard enough to be able to perform for two people. So figuring out how you can manage performance anxiety ahead of time is a good idea.

Good luck!

Advice – My husband didn’t react well when I told him that I wanted to find a new career.

January 5, 2021January 4, 2021 / teatimewithtomato / Leave a comment

I have a career where I make good money. But it is an hourly position with no pension or benefits that tie me to it. I also have “side gig” that I love and enjoy, but obviously make less doing. I discussed my desire to further my learning, maybe take some courses, even start my own business this year, or at least move in a direction that will get me closer to my own personal happiness. We have no financial stress, he makes good money, we have rental properties that cover most of our own personal bills…

His response was just to keep doing what I’m doing, that’s it’s good money, he doesn’t just quit his job because he doesn’t love going every day.

The conversation didn’t end well, I got upset, we both got a little defensive, and I’m just feeling really really let down.

How do we get past this?
Emma, Reddit.

Dear Emma,

Let’s first take a quick step back and review what happened.

In the cusp of a new year, you looked back upon your current financially satisfying but personally dissatisfying career. And when you decided that you wanted to expand upon your personal growth by exploring a more personally rewarding career or enrolling in personally enriching courses, you communicated so with your husband. And instead of nurturing or engaging in the type of constructive dialogue you wished to have with your spouse, he got defensive about your desire to keep growing.

It is no wonder you feel disappointment and sadness from that interaction! Disappointment is the gap between your expectation and your reality. And you might have had a very different expectation of how that conversation was going to go than how it actually went in reality. You did expend quite a bit of emotional labor on what you wanted to accomplish in the new year, long before you approached your husband. And when you did come to him with what you have internally processed, you already knew the gravity and sincerity of what you wanted to communicate with your spouse – the very gravity and sincerity your husband appear to have missed or misunderstood. That is where your pain is coming from.

And I think that is the best place to start your next conversation with your spouse.

Even you acknowledged within the very first sentence that your current career is financially rewarding. But your career dissatisfaction is a deeper reflection of your personal desire to keep expanding upon your foundation, not as a reflection of how much money you earn from your hourly job. And it could be possible that your husband could not or did not see how much of a role your personal dissatisfaction played in your overall dissatisfaction with your current career.

A good way to help your husband understand how you feel is to relate his actions and words to how you felt. When your husband dismissed your desire to take new courses, you felt disappointed. You currently feel very disconnected as a result of the last conversation with your spouse. It could be that his intent wasn’t necessarily to be dismissive or defensive. Perhaps his emotional hygiene was cluttered with other aspects of your collective lives together that disconnected him from being fully present in that vulnerable conversation with you. But your recollection of that memory – the feelings they brewed – are just as valid as his recollection of his words.

Here is an exercise I believe you can implement into your next conversation with your spouse about your intention to expand. Try having your husband explain to you in his own words where he thinks your headspace is at. Relating to others and teaching others is one of the most effective ways for us to learn and absorb new information – 90% of new information, actually. And he might have a better time understanding the gravity and sincerity of your intention setting if he had an opportunity to empathize with your deeper desire to grow in his own words. After all, this is your own experience and reflection. Clearly, your husband has a different relationship and experience with his own career. It is important for him to acknowledge and understand that your experience with your career is not at all the same from his experience with his career.

It might be a good practice for you to also take on his role in this conversation. Try and speak out loud what you thought he felt during the conversation and gauge where his deeper motivation or insecurity could have stemmed from.

If the first step was for your partner to validate your feelings and intentions, then the next step is to figure out why this happened and how you can avoid this type of disconnect in the future.

I am curious if there have been any other instances of obvious communicative disconnect in your relationship history with your husband. We only have a smallest slice of your relationship at this specific conflict point. So you might have a better idea if this is a next example in a general dismissive pattern or if it was a truly random one-time occurrence from an otherwise attentive partner.

It is also very important to note that we are all experiencing a massive societal trauma through this pandemic. We are all on edge, pushed to the brink of our own respective sanities. So it could be possible that your spouse just did not have the adequate emotional capital to process what you shared in a meaningful and productive way. Explicitly allocating time and space for a discussion of this magnitude might be a good way to avoid this type of miscommunication in the future.

I’ll leave you off with one last consideration. In each of our engagements, we sometimes make emotional bids for our partners. Gottman Institute defines emotional bids as “the fundamental unit of emotional communication” where we request to connect with our partners in an emotional, physical, or sexual nature. This video explains emotional bids in more detail. In your case, your partner turned away from the bid you made, which prompted you to retaliate in defense of your vulnerability. It is important that both you and your husband acknowledge and understand that what happened was not okay, before you two can even attempt to reconnect and rekindle over this miscommunication.

Good luck!

Advice – Is my bisexual girlfriend polyamorous?

December 29, 2020December 29, 2020 / teatimewithtomato / Leave a comment

My (33m) girlfriend (26f) and I have been together for about a little more than 6 months and everything has going smoothly between us so far. But there has been something that doesn’t sit quite right with me.
To give you some background, we met on Tinder and after having sex a few times told me she had to break up with the other guys because we’re on the same wavelength. We just clicked. Then she asked me to be her boyfriend after dating for a few months.

We have had a few discussions about our relationship boundaries and expectations in the six months we have been together. We have decided to stay monogamous, but every conversation that we’ve had about the subject has not left me feeling very reassured about our future. For example, she has mentioned polyamory during a couple of conversations but not that she actually wants that to be part of our relationship, she just mentioned it when talking about how well our communication is. I told her that wasn’t something I was interested in and she said she was not either but again mentioned that if it did come up she knows we could communicate. So it has left me confused because she sometimes posts pro poly memes and quotes on her social media and follows a page called poly.land. She says she wasn’t interested in that and that when she was on Tinder dating guys she was sort of already getting that experience.
We had another talk about our relationship recently because I guess I’m not feeling reassured that we’re not going to change away from monogamy. She got a little upset that I wanted to talk about it again since she said we already “agreed to remain exclusive to each other until we decide to change our relationship agreement” and that last part left me feeling confused but I don’t want to bring it up anymore and try to take her word. Another detail is that she is bisexual and has only kissed a woman but never slept with one and I’m thinking she is still open to making a connection with one if she finds the right one. Also, she told me there was a girl she liked while she was with her baby daddy but he was abusive towards her and she wanted to leave. Basically, it all just seems like she is still making herself available to women and our conversations have not reassured me that we will remain monogamous in the future.
Is she open to the possibility and maybe not sure that is what she wants or is she waiting to see how things go with us?
Help Me I’m Frozen, Reddit.

Dear Help Me I’m Frozen,

There are quite a few misconceptions around polyamory and bisexuality that I believe that we should first spend some time deconstructing and analyzing before we can get to the meat of the advice.

First things first. Being cognizant of polyamorous lifestyle is very, very different from being in polyamorous relationships. And being in polyamorous relationships can look very different for a person who is more ambiamorous (as in ambivalent about polyamory/monogamy) and for another who is strictly polyamorous (as in cannot ever do monogamy).

And let’s talk more about being polyamorous as compared to doing polyamory. I am a firm believer that too many folks use the identity “polyamorous” to forsake the emotional labor that accompanies ethical non-monogamy. It is a serious problem in the poly-spaces I reside in because that poly label is frequently misused by people who aren’t ethically non-monogamous. It is often a much more fruitful endeavor to ask “Can I do polyamorous relationships?” rather than “Am I polyamorous?” The first question allows us to inspect the context of the relationship landscape as well as pre-existing relationship agreements, whereas the second question often lends itself to a much higher burden of proof. The current exclusive relationship agreement in your relationship does not allow for any non-monogamous arrangements. And since she is clearly aware of polyamory, she is consciously choosing monogamy with you when she agreed to be exclusive with you. And it even sounds like she has continued to reemphasize her stance on exclusive monogamy with you.

Another thing for you to consider is that there are positive aspects to polyamory that are absolutely applicable to monogamy as well.

In my opinion, Poly.land is a great blog that talks a lot about poly-specific and poly-adjacent materials that doesn’t just provide value for staunchly polyamorous folks but also for staunchly monogamous folks who want more information on how to improve their own monogamous relationships. And perhaps that is what your girlfriend is doing by acknowledging and celebrating polyamory even if she doesn’t ever want to do polyamory herself.

As your girlfriend noted, one of the things that polyfolks seem to do well is in communication. Many polyfolks I know do intensive monthly check-ins similar to the RADAR model from Multiamory to address relationship conflicts, engage in each other’s vulnerabilities, and keep each other accountable for necessary personal developments. And it sounds like she wanted to celebrate the communicative strength in her monogamous relationship with you, similar to what she has read about in polyamorous relationships. And instead of acknowledging that bid and diving deeper into how your communicative chemistry is on par with those of polyamorous relationships, you immediately jumped to reject polyamory and get defensive about some underlying insecurity that you might have.

See how that is ironic considering she initially approached you to celebrate your communication skills?

If you dig deeper into why that feels so sore and so sensitive, you might find that there is an underlying fear of the unknown. Specifically, it is a fear that she might change her mind about monogamy. In a later comment, you mentioned that you would like your girlfriend to be upfront and clear about any future intentions to be non-monogamous. And it sounds like she already has. She did exactly that when she said she “agreed to remain exclusive to each other until we decide to change our relationship agreement.” It could be that you aren’t hearing what she has to say; that even though she knows about polyamory, she is choosing monogamy with you.

Even your internal dialogue and subsequent projection about her own bisexuality is rife with misunderstanding and reflects on your deeper insecurities.

I wrote a column about the intersection between bisexuality and monogamy in this post from a year ago. And in that post, I specifically talked about how bisexuality can and often does exist in the same space as monogamy. Bifolks need not be in multiple relationships with people of different genders in order to be a card-carrying member of the Bisexuals. Bifolks who are in a monogamous relationship with same or opposite sex partners are still bisexual. In a more recent column from about a month ago, I wrote about how the number of same sex partners do not define bisexuality; bisexuality is justified in the mere virtue of its existence. What I am trying to say is that she is still choosing to be with an opposite sex partner – like 84% of the bisexuals who end up in opposite sex relationships. And her choice to be with you does not diminish or reflect negatively on her bisexuality.

You say that you think “she is still open to making a connection with one if she finds the right one.” That is completely contradictory to both what she has agreed to with you and what she has shared about her sexuality. Consider that straight folks have crushes on opposite sex friends and coworkers too. And crushing on people is natural. Exclusivity does not mean that you won’t have crushes on other people. Exclusivity just means that you will develop proper boundaries to avoid indulging in those crushes. In the same way, just because she is bisexual doesn’t mean that she can’t make close connections with people of genders that she happens to be attracted to. And part of building upon a relationship is to develop that trust that your partner will honor all the relationship agreements even when you aren’t omnisciently present in all of her personal connections.

It is deeply problematic to override her own experience of bisexuality into how she wants to experience her romantic relationship with you.

How you have internalized her bisexuality is not at all how she herself experiences her bisexuality. It is not your responsibility to comprehensively understand what her bisexuality means for her. It is however your responsibility to acknowledge and accept her sexuality as she experiences it.

It is time to fix the broken bucket.

There is a popular Korean proverb that goes like this –

안에서 새는 바가지 나가서도 샌다.

It strictly translates to “A broken bucket that leaks inside will also leak outside.” And in the same way that a broken bucket will never hold water, all the reassurances your girlfriend can possibly pump into you will hold no water as long as it leaks through the fundamental holes that are your deeper inner insecurities.

Consider all the information you have in front of you. You say that you don’t feel reassured. But it isn’t really your girlfriend’s responsibility to make you feel reassured. It sounds like she has already done a lot to make you feel reassured. But that relationship anxiety that you feel is very likely coming from deep inside of you, a part of you only you can alter and make changes to. It is manifesting in the insecurity you feel about her potentially changing her mind about monogamy. It is also manifesting in the way that you envision her bisexuality to mean something else. Take time to acknowledge these as growth opportunities that you need to work on either by yourself or with a trusted therapist.

As you have experienced, continuing to revisit and re-trigger these conflict points with your girlfriend will not go well. The remaining work is yours and yours alone.

You say that you want to take her at her word. So take it.

Good luck!

Advice – Should I tell my girlfriend I slept with other people while we were on a break?

December 22, 2020 / teatimewithtomato / Leave a comment

For clarification; we’ve been dating on and off for about 8 years and she is my best friend.

A couple of years ago we had a year or so apart, she broke up with me. We still had some same friends so we saw each other around on and off through that time and around a year or so later we got back together and are together still. We are as strong as we’ve ever been and there is no immaturity about it all.

In our time apart I did what any newly single person would do and had fun, met up with people and had a few drunken ONS. But I never mentioned it to her, as we were not together ofc. And haven’t since then, I didn’t bring it up when we got back together.

However, in a jokey game recently with friends where we had to answer questions about each other to see how well we knew each other, the number of people each of us has slept with came up. I didn’t correct her number she gave me, mostly because I didn’t want the first time she hear about it to be in front of friends, when were having fun etc.

It has played on my mind a bit all this time. The line between being honest and being too honest.

Would bringing it up, long after the fact, be pointless?

Or would her finding out through other means, and me having not told her, be worse?
Anonymous, Reddit.

Dear Anonymous,

I understand your initial decision not to tell your girlfriend about who you slept with in the year apart. It is possible that you didn’t feel the need to disclose how many partners you slept with for couple different reasons. The safe and obvious assumption from when you were apart from your girlfriend is that both you and your girlfriend found others to meet your sexual needs for that year. In addition, you might not have been emotionally prepared to hear how many people she slept with while on break, even if you operated under the assumption that you both slept with others.

Your recent decision to not correct your girlfriend also makes sense. Not only would it have been incredibly humiliating in that specific circumstance, I agree with you that it would not have been a safe place to openly talk about vulnerable topics. This in turn explains the retrospective ambivalence and guilt you feel about not being upfront about your sex life during the break. This current ambivalence and guilt stems from the initial decision to not share, because at least a small part of you believed that you should have shared.

As you pointed out, there is a very fine line to toe between being honest enough and being honest to a fault. And the thing is, that fine line varies wildly between person to person. There is no universal morality around when or if you should talk about your previous sexual history with your partner because it greatly depends on your overall comfort level as it pertains to discussing previous sexual experiences, the context of that discussion, and your personal intention leading to that conversation.

Another wrinkle in this circumstance is your intentions.

If you sit back and reflect on why you want to share your sexual history during the break, you might find that the inherent ambivalence flows deeper into each of those possible intentions.

If your intention is that open and honest communication should be always be exercised, then you might find yourself contending with the decision you’ve already made not to share. The difference here is clear. Timing is all different. You might not have known back when you got back together that you would continue to stay together. And for those couple years, you were able to build upon the baseline of trust that you had before you two decided to went on a break. And so, because the context of your decision back then was different from the context of your decision now, this decision need not be the same.

Your intention could also be brewed with the desire to gain control over the narrative of your own sexual history. Built into the initial assumption of sexual activity during break are two separate foundational beliefs. The first belief is that you and your girlfriend were on the same page about your respective sexual activity during the break. The second belief is that you and your girlfriend would each inform the other any aspects of your sexual history without each other, if it was deemed relevant. As such, your desire to correct the wrong comes from a deeper place where you want your girlfriend to live in the same reality as you do. That is both fair and sound.

However, if your only intention is that revealing the full extent of your sexual history will alleviate your feelings of guilt, then that is neither a compassionate nor safe way to approach this revelation for your girlfriend. After all, your girlfriend could find her anxiety and insecurity triggered to hear that she wasn’t exactly on the same page as you for the past couple years.

What is the ongoing price of admission that you are willing to pay to keep this hidden from your partner?

Your decision will also have to reflect your girlfriend’s headspace.

How has she handled learning about your sexual history or general sexuality in the past? If the overarching modus operandi regarding sexual history in your relationship has been a more of a Don’t-Ask-Don’t-Tell approach, then the risk of unknown and the risk of negative reaction greatly outweighs the overall benefit of alleviating your guilt and true honesty about the past. However, if she has taken talks about your and her sexual history well in the past, then this conversation could absolutely be an opportunity for you and your girlfriend to connect deeper as a couple and as individuals.

I sometimes jot down my own thoughts down on paper (or screen) as a way to have a dialogue with myself over complex decisions. On paper, my idealistic self would outline all the good a potential decision might bring. Then I would sit back and talk back in person to my idealistic self all of my worries and fears about that decision. And this back and forth would go on until I decide that either:

The overall goodness of the decision outweighs the possible badness, at which point I push ahead with my decision.
The possible badness of the decisions outweighs the overall goodness, at which point I take time to grieve through the decisions unmade.

My two cents: take this opportunity to develop yourself or your relationship. If that means sharing this very vulnerable and neglected part of your past history, then use that momentum to share why this felt so vulnerable to share and connect deeper with your girlfriend to explore other vulnerable spaces. Even if this doesn’t go well, you can still use this as a learning lesson for yourself on the boundaries of your and her fine lines on honesty.

Good luck!