Hi Captain Awkward,

My partner [26M] and I have been together for about 6 months. We both genuinely love each other, and have been telling each other that we love each other for the last few months; but some recent events have led me to reconsider how seriously committed he is to the relationship, and how much I can trust him.

All of this started about two months into our relationship, when he invited me to his roommate’s brunch at his apartment. He introduced me to a friend of his at the brunch, let’s call her Sophie. It was immediately obvious to me that they shared some sort of a romantic history, for the following reasons: 1) Sophie felt comfortable flirting with him in front of me, 2) she wouldn’t make eye contact with me when we were all engaged in a conversation together, and 3) she made a rude joke about me during this three-way conversation that was frankly quite demeaning (accusing me of being afflicted by a psychological syndrome). I didn’t say anything to my partner at the time because we just started dating two months prior (and I didn’t want to come off as jealous/possessive/controlling), and we hadn’t officially talked about being boyfriend-girlfriend yet (although other events at the brunch sparked the wonderful conversation which resulted in us making it official, two days later). So I decided to brush it off.

Fast-forward about two months later. My boyfriend kept inviting me to parties/get-togethers that Sophie was throwing, and I kept declining. (I gave excuses, but I should’ve been forthright about the fact that I didn’t want to go to an event with someone who I suspected he shared a past with, and who felt comfortable flirting with him in front of me). He ended up going to her birthday party one night. When he came to my apartment later that night, I finally built up the nerve to confront him about whether or not they shared a past. He said yes. Here are the many red flags that popped up during my partner’s recounting of said party:

At this party, her and her friends filmed a movie reenactment, including a scene where my partner kneels down on one knee, grabs Sophie’s hand and kisses it tenderly. My partner showed me this video with pride and laughter once he arrived at my apartment later that night. Important note: Although there were many parts to this video (approx. 7), which all appeared on Sophie’s Insta story that same night, the only part of that story that she *permanently posted to her public Instagram profile* was the video of my partner kissing her hand.

My boyfriend revealed to me that they spoke at the party about their (almost) romantic past (they went on a date and almost hooked up once on a separate occasion, but they never pursued anything because Sophie was “interested in something casual” and he was “interested in something more.”).

Sophie asked him if he “made me his girlfriend yet”, to which he said yes; which was followed by “are you two exclusive?”. When my partner said that we were indeed exclusive, he explicitly reported that Sophie reacted in a “disappointed way”.

Just before my partner left the party, Sophie grabbed his phone and sent me a selfie of the two of them together (despite my not knowing her? It was strange.).

Breach of trust #1: Not telling me about his romantic past with this “friend” of his before inviting me to multiple events that she was throwing

After this all happened, my partner and I had a long conversation about boundaries. I explained to him that it makes me uncomfortable to be around people he shares a romantic history with; and that, because I’m the kind of person that prefers to remove myself from situations where I feel uncomfortable, I *need* to know this information before making a fully-informed decision about whether or not I want to show up to a social event with said person. (I can’t very well tell him who and who not to be friends with; all I can do is decide where I want to go and who I feel comfortable surrounding myself with). I also explained that Sophie’s behaviour was especially problematic, because she feels comfortable actively flirting with someone who she knows is in a relationship (not to mention– flirting with someone who is in a relationship [my bf] *in front of* the person they’re dating [me]).

At the time I thought the conversation went really well. My boyfriend was receptive to what I was feeling and saying, acknowledged that Sophie was indeed flirting with him, and promised to tell me in the future when invited to a social event if someone he shares a romantic history with would also be there. Everything seemed to be going well until the last couple of weeks, especially until last Sunday…

Some context is in order here: my grandmother passed away two weeks ago, and her funeral was last Saturday. I also found out that I was pregnant the morning of last Sunday (I’m getting an abortion). I was out of town for the last two weeks to help with the funeral and such, and during this time my boyfriend fell into radio silence. We did speak every now and again, but he was far from supportive during this time. Even worse, when the test came out positive, he waited three hours before contacting me; and when he did, he didn’t even acknowledge that the test was positive.

Okay, back to the main narrative: on Sunday afternoon, I received a notification that I was invited to my boyfriend’s birthday party. I checked the invite list, only to find that Sophie had already clicked “going” on the event.

Breach of trust #2: Invited Sophie to his birthday party (which indirectly uninvited me) *despite* me telling him that being around Sophie makes me feel really uncomfortable [context adding insult to injury here as well].

I was pretty devastated to say the least (and especially, in the context of grieving the loss of my grandmother and having to deal with an unwanted pregnancy). I called him that night to explain to him why I felt hurt, disrespected, and disappointed. I explained that I would not be attending his birthday party, because his inviting Sophie indirectly uninvited me. I explained that this shouldn’t be a surprise to him, because we had a conversation explicitly about this and explicitly about her. I explained to him that I was hurt because he was prioritizing his relationship with Sophie over his relationship with me. (I can go into more detail about the conversation we had in the comments section if need be).

Anyways he apologized, and went so far as to cancel his birthday party (which I thought was a bit drastic, but OK it’s his decision). He’s since seemed to *actually* realize how inappropriate Sophie’s behaviour was, and has admitted that “he didn’t want to see the bad side of her behaviour when I first brought it up because he likes to see the best in people.”

Breach of trust #3: Less than a week after the birthday party fiasco, after I explicitly asked him not to tell his two male friends about the pregnancy, he told them anyways. He (again!) apologized after the fact, but this is another installment in a set of trust breaches that has sounded two many alarm bells in my mind.

Part of me thinks that my boyfriend is actually interested in Sophie, and that’s why he’s been enabling her flirtatious behaviour all of this time (despite saying multiple times that he isn’t interested). But part of me also knows that I’m thinking these thoughts because I have lost trust in him, and I don’t know how to rebuild that trust. I’ve had a conversation with him about open communication, teamwork, and honesty in relationships since BOT #3. A huge part of me, the “pessimistic” side I guess, still doesn’t believe that he’s going to put in the effort to change his behaviour and to become more trustworthy a boyfriend. That’s why I’m here… for advice on how to think and how to act going forward in this situation. I’ll provide more details in the comment section if need be, don’t feel shy! Thanks all in advance.

Sincerely,

A Confused 23yr old she/her

Hi Confused and 23!

I’m so sorry for the loss of your grandmother, how upsetting on top of everything else.

Here are some big things I’m seeing in your letter:

You’ve only known this person for six months.

He is not careful with your feelings.

Whenever there is a situation where he could choose to respect your wishes, he…forgets…what they are?

When there is a stressful life thing that you are tackling, instead of supporting you, he…ignores…you? Gotta be honest, “There was a death in my family and the person I’m in love with responded with ‘radio silence'” is not what comes to mind when I think about what the Great Loves Of One’s Life might look like.

He apologizes, but he doesn’t learn. He handles conflict by telling you what you want to hear in the moment and then doing exactly what he said he wouldn’t do.

He handles conflict by telling you what you want to hear in the moment and then doing exactly what he said he wouldn’t do. You’ve only known this person for six months and, whatever his many fine and attractive qualities might be, we already know that he is not great at boundaries, not great at respecting (or even remembering) your wishes, not great at preserving your privacy, not great at showing up for you, and he continually seeks the company of someone who aggressively flirts with him and who blatantly tries to squeeze you out of the picture.

Even if we assume your boyfriend always acts with the best intentions and genuinely doesn’t mean to upset you, there is a kind of cluelessness and clumsiness that is indistinguishable from malice. The word that keeps coming to mind is “feckless.” At minimum, this guy is feckless. At minimum. He’s also evasive? Slippery? Conveniently forgetful?

As I see it, there is one person besides you in this situation who is being entirely transparent and consistent in their behaviors and intentions. Unfortunately, that person is Sophie (whose video/Instagram trick/text message trick should win some kind of Captain Obvious Award for Attempted Dramatic Annexation, truly that is next level work).

I know that cutting this dude loose feels like letting Sophie “win,” and that feels unfair, but I also think the right partner(s) for you in the future are going to be people who can see through antics like hers and be straightforward about all of it. What you need and deserve is a partner who can say (to you) “Yeah, Sophie had a thing, or we almost did, she can be really blatant like that, I’m so sorry, that was a gross thing to do and I’m sorry I participated in any of it, and I definitely should have warned you” and say (to Sophie) “Look, your interest is flattering and maybe if we’d figured this out way back when we could have had something, but that moment passed long ago. I’m happy and in love, so back off, and if you’re supposedly my friend you must stop being rude and weird to my girlfriend!” then also skip inviting her to things for a while.

Not because you’re some caricature of a controlling girlfriend who polices your partner’s friendships, but because if you correctly sense that something is complicated or “off” with a particular friendship, your theoretical future partner should have enough emotional intelligence to register when the “Sophies” of the world are NOT acting like friends and when everybody could benefit from some space and time to regroup into their best selves.

As mentioned often in this space, I don’t think people have to be friends with exes or past hookups or people where there’s been a strong pull or possibility, or that everyone should even try. But people certainly can, when it’s been possible for me it’s frankly outstanding, and I know from experience that people with complicated histories and longings actually can go on to have healthy and awesome interactions someday. Want to know what makes any of that possible? First, it’s honesty, but not JUST honesty, not the kind that’s like “Of course the Fae can’t lie in response to direct questions, so I just made sure you never asked me any” or the kind that’s like “Well I didn’t technically lie, I just didn’t happen to mention it, but ok, you’re right, when you mentioned it I did technically act like the whole idea was ridiculous, but come on, when you finally dragged it out of me I told the truth, you can’t be mad! I was honest!” I’m talking actual honesty, honesty that is forthright and respectful, honesty that gives you the information you need to consent.

Making friendships-with-history work also involves a shared adult understanding that “friend” isn’t just a word we use as catch-all for people who we don’t want to fuck at this exact present moment, like once you say that word everyone in your life is just supposed to go “Oh, the lady who directed a short film on her birthday primarily so that you would have to kiss her and then weaponized that clip against your girlfriend using both social media and text and then kept asking you if you and your girlfriend were ‘really together’ is Just A Friend, cool, yeah, it’s obviously unfair for anyone to have reservations about that, carry on.” The more I think about this incident, the more ridiculous it seems. You’re 23, everyone in your story is probably pretty young, but you’re not “This is an episode of Glee and we’re trying to get to regionals” young, are you really supposed to fall for the “let’s put on a play, it’s all innocent fun!” gambit? No.

More generally, if you start dating someone new and their social circle is teeming with exes and unfinished business and hushed conversations and you leave every gathering with a strange feeling like “Am I imagining this or is partner’s ‘friend’ I just met trying to undermine me in some weird way?” consider: Is this a) a cool new relationship or b) the setting for a trashy vampire novel? No shade against trashy vampire novels, some of my best reads are trashy vampire novels and some of my best friends are trashy vampire novels waiting to happen, but haven’t we all met That Person, the one who is only friends with people they want to sleep with (or used to sleep with or almost slept with but didn’t…yet), the ones who look you in the eye and reassure you that all these people are “just friends” and “don’t be jealous, darling,” and maybe they never actually do cheat on you during the actual time you technically agree to be exclusively together, but the possibility is always there, watchful, communicating only in in-jokes and“Oh, nobody you’d know,” hugging too long and smelling each other’s hair and most/worst of all reminding you that should your needs ever get too needful or your boundaries get too fence-like, your charismatic new love interest has other options. I think there are people who thrive on this kind of thing and I wish them well in life but holy shit do I wish I had learned to spot them earlier than I did. They make for interesting bedfellows but not comfortable ones, you can get shredded right in front of them by their so-called “friends” and never be certain they even noticed the blade. You’d be surprised how much damage someone can do without any of it ever being precisely their fault.

Or maybe you wouldn’t, Letter Writer, since it’s only been six months since you met your boyfriend, you are unhappily pregnant, reasonably jealous & suspicious, grieving, your privacy has been hung out to dry by a person who is supposed to make things easier and better for you and who was told, clearly, with words, exactly what you needed. And on top of it, he’s avoiding your texts. You’ve lost your trust in him for a reason and you asked me how to rebuild it, but I can’t in good conscience tell you anything that is likely to work. You weren’t the one who broke the trust that was forming between you and frankly, you’re powerless to fix it. He’s the one who would have to do the work, he’s the one who would have to continually demonstrate growth and trustworthiness and learning. You could of course pretend that everything you experienced didn’t happen the way it did, you could try your best to create a fictional dreamworld where you let him start over from scratch, like a snow globe that you can shake and reset, shake and reset, one you clasp with increasingly white knuckles as you keep hoping that he’ll rise the occasion for fucking once in his life. Even then, he’d have to, idk, text you back?

The heartbreak of it is that you love him. The heartbreak of it is that maybe he will grow up and improve, with enough chances, maybe he means it, maybe he wants to do better. And if you break up now, you’ll never know. That hurts, and I’ll never tell you that hurt isn’t real, that the grief we feel when we love someone who isn’t right for us and choose to let them go doesn’t matter. What I will tell you: It passes. It heals.

I’ll also tell you that you are too precious and lovely, you are worth far too much for me to advise you to bet any more of your irreplaceable time on someone who has been so careless with you.

In closing, my actual recommendations are these:

Break up with this guy, grieve for what might have been and what you felt for him, but let him go. “This isn’t working, let’s break up” is a useful script, maybe the less said the better right now.

Surround yourself with true and trustworthy friends. Hopefully one of them can hold your hand before and after your upcoming medical procedure* that sounds to me like a very wise and useful and good way to take care of yourself right now. May that all go extremely smoothly.

Thoroughly filter and block off your social media so that when the inevitable news of your ex and Sophie celebrating their instant rebound with their Instacart groceries braising in their Instant Pot on lands on Instagram it won’t even be a blip.

Be very, very good to yourself.

*Moderation Note & Policy Reminder:

I am allowing comments on this post, as I think people will have lots of valuable insights on trust and breakups for the Letter Writer and it’s been a while since we’ve had a good “Disappointing People And How To Dump Them” thread. I thought about deleting the abortion information from the letter to make this all easier on myself, but screw that, Letter Writers and community members are allowed to talk about abortion as the routine, sensible medical procedures they are without apology and without dealing with a creepy onslaught of stranger-feelings or debate club antics.

I assume it’s clear by now that I think that people who can become pregnant should have safe, free, convenient, frictionless access to every possible avenue to make their own medical and reproductive decisions, but in case that was somehow unclear: The official policy of Captain Awkward Dot Com is that abortion is good and useful.

If your personal ethics or beliefs prohibit abortion, I support your choice to never have one! You’re the boss of you and your body and your situation, nobody gets to yell at you about your private medical choices. I’ll even throw in doing whatever I can to vote for and advocate for policies that make pregnancy and the choice to be a parent more affordable, safer, and more possible for everyone in my country who wants to choose that path.

Still, let me be absolutely clear: You are the boss of your body and nobody else’s. I am the boss of this website and I do not have to hear out “both sides.” Attempts to persuade the Letter Writer about her medical care or “debate” reproductive rights, comments that have even the merest whiff of being weird and overly interested in that aspect of things will be deleted, though you should feel absolutely free to share your thoughts here, where they’ll do (me) some good.

In closing, please keep comments kind, focused, and on-topic (The topic is handling disappointing people who break your trust. Do you break up? Anybody got a good story for something that actually worked to rebuild the relationship?). Thank you, and love to the Letter Writer and all who are jumpstarting this year’s International Women’s Day celebrations by cutting loose unworthy boyfriends in order to focus on World Peace.

March 9: Comments are closed! Thank you!