Advice – I feel insecure about my boyfriend’s past fling / friend.

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/u/jdkman238 writes on /r/relationships…

“I [25F] have been with Brad [27M] for about 6 months. We spend a ton of time together, and for the most part, I’m very happy with our relationship and see a future with him. The only thing that gives me pause is his relationship with a friend of his, Ashley [20sF].

He was transparent about their history from the beginning – they met on Tinder (as did we), casually dated/hooked up for about a month, until he decided that he was not interested in pursuing a relationship with her and asked if they could just be friends. She said yes but still had lingering feelings for him. This smoothed over once she started dating someone else, who she is currently with.

Since then, the two have developed a friendship and will do things like get lunch together sometimes, play board games with mutual friends (Brad always invites me), casual things like that. I have never noticed any appropriate or flirty interactions between them, but she has always been kind of cold and awkward around me. To be fair I’m sure she could say the same. It’s just…kind of weird to me, honestly.

The two text fairly often – oftentimes when his phone buzzes, it’s a text from her. Again, I’ve never seen anything inappropriate. He is slightly protective of his phone, maybe because I’m always glancing over at his screen. Even though he has never been dishonest with me (that I know of), I’m worried that there could be more to their friendship that I don’t see. Just due to the nature of their past.

I want to ask him to look at their text messages for peace of mind, but he hasn’t done anything suspicious and I’m worried he would get upset that I don’t trust him or something. I really do want to but I feel like it’s a big ask because of their history and their closeness. What do you think? Is there a better way to address my anxiety about this?”

TL;DR – My partner is close friends with someone he once had a romantic/sexual past with. He hasn’t given me reason not to trust him, but I can’t just get over the worry that their relationship isn’t purely platonic. I want to ask to read their texts to be sure, but wonder if there’s a better way to go about it.

Dear JDK Man 238,

I hear your concerns. But I do think that your intentions are not completely clear and appear to be motivated by your deep sense of insecurity about their connection. You’ve been with Brad for six months. And as you said, he has been very transparent about his connection with Ashley the entire time. And based on what you said, there hasn’t been any indications of unethical behavior.

There are two points to outline here before we get to the meat of the advice.

Brad’s connection with Ashley is for his to maintain. It honestly sounds like he has been doing a good job of maintaining his respectful boundaries to make sure neither he nor Ashley does anything unethical. That means you have to leave that connection up to him to manage, and trust that he’ll continue to manage his boundaries around her to the best of his own abilities. After all, he was the one who de-escalated their sexual connection down to a purely platonic one. I don’t see any evidence to doubt his mindset.

Second point I would like to make is that your connection with Ashley is for you to maintain on your own. You mentioned that she has been a little weird and awkward around you. Can ya blame her? You’ve been weird and awkward around her too. And that kind of negative mentality cycles and contributes to a negative feedback loop. You might never be fully comfortable around Ashley the way Brad appears to be, because you have some personal hangups around their previous history. But regardless of whatever has happened between them, it is on you to forge your own connections and work on your own friendship with Ashley (should you decide to). Otherwise, her discomfort can easily be explained away by your own discomfort reflecting and projecting off of her.

Photo by Miguel Á. Padriñán on

I think the most important point to make here is that you are more concerned his reaction to your ask than the fact that you can’t fully trust him.

Trust is earned, not asked for. And he has done his best to earn your trust through your six month relationship. What exactly would reading through six months worth of his text exchange with Ashley accomplish for you? What do you think it’d accomplish for Brad? Would you be comfortable asking for this consent from Ashley who also has to have her share of text exchanges revealed to you?

You asked about how to better address this anxiety you feel. First step is to own that it is your anxiety speaking. That tape is playing from inside of you. If you really are feeling that insecure about Brad’s connection with Ashley, why not take that next opportunity to play some board games with them? Try to see Ashley as someone other than someone your partner used to sleep with. See her for the human that she is. She is clearly a close friend of Brad’s. She at least deserves a bit more of your time and energy.

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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