Question # 164: Redrawing boundaries with a possessive ex.

Dear Captain Awkward:

I’m a transman – reasonably attractive, fairly extroverted, early in my transition. I have recently moved to a new city and found a group of people who are both awesome (sharing similar interests and drives) and supportive of my transition. I even started dating a nice young man in this group. Then he called it off. We took time apart. I was distressed, but realised I’d rather have his friendship than nothing because he’s important.

Since then, however, he’s been flirty, possessive (both verbally, when someone else hits on me, and by keeping my things), mis-gendering me publicly, and generally a combination of acting like a jock out of an 80’s movie and like we’re still together. It’s unattractive, unlike him, and causing me a lot of distress. I’ve tried talking to him and it feels like, short of cutting myself out of our shared friends circle, I’m stuck with this. He’s even telling people that we’re still together! I am stuck looking like the asshole who can’t deal and I am at a loss.

At a Total Loss

Dear At A Loss:

I am so sorry this is happening to you, and that it feels like a choice between your own safety and comfort and your new-found friends. You are correct that if he keeps doing this and your other friends won’t check him or back you up, you will have to leave the group. It is heartbreaking and unfair.

A lot of people will jump in and say “DTMFA!” “Get new friends who appreciate you!” and yes, it may come to that, but I won’t insult you by suggesting that’s an easy thing to do especially when you are in a new city. Those of us who live away from our families create families with our friends. Those relationships are primal and very important, and they can change and grow and survive hard times if there is love and a willingness to work at it.

So what I have for you is less a script than a month-or-two-long campaign to try to make this a little better for you and give all of these friendships a chance. I want you to build bilateral ties with other members of the friend group (so he’s not your closest connection), I want you to tell some of them frankly what’s going on and ask for help/advice in managing him. I want you to avoid him for now to the extent possible – you’re working up to another serious talk, but that’s a ways away. And I want you to take a few tiny steps toward meeting some different/new people, so that you are not so caught up in this one group and not so dependent on them.

Step 1: Invite people in the friend group to do things one-on-one with you outside your usual hangouts. If they are GSF#5 carriers, this may take some effort on your part, because they will automatically want to text everyone and make it a group thing, so go slow. They are your new running buddies, people you take a class with, laundromat partners, you-just-happened-to-make-too-much-dinner,-would-they-help-you eat-it? friends. The first time you hang out with them, you don’t need to necessarily get into your whole history with your ex. Keep it light and free of an agenda beyond wanting to spend some more time with them and get to know them better.  Save serious talks for the second time you hang out one-on-one, unless they ask you, in which case you lay it on them.

That script is what you told me:

I really adore ___, and he and I were so close, but he’s making me very uncomfortable with some of his behavior (possessive, mis-gendering, telling people we’re still together when he is the one who broke it off). I’ve talked to him about it, but he won’t knock it off? Has he acted like this before? How do you think I can get him to stop?”

And then, if that conversation goes well, and you feel like you can trust the person, you ask for what you need:

It would help me a lot the next time he behaves like that around the group if someone would step in and just say ‘Knock it off,’ so I don’t feel like it’s just me and I have to be the weirdo.”

Then let it drop. Act like you assume they will be cool, and that things with your ex will be cool. Chances are they have noticed something awkward and weird going on, but maybe didn’t know how to react before or didn’t want to get in the middle of what seemed like a lover’s quarrel, so you’re telling them exactly how to react.

If they try to put you off with “Well, that’s just (your ex), you know what he’s like” and brush off your concerns, they’ve indicated that they are outside the circle of trust.

Step 2:  Pull back a bit on The Gang’s All Here Events for a few weeks. Go to every other one. And when you do go, give yourself a time limit and an easy out. See your friends, have a good time, but as soon as things start to get weird with your ex, extract yourself. Here’s a big one:  Limit your own alcohol consumption, and leave before others (especially your ex) have had a lot to drink.

Step 3: Speak up for yourself. Start with “Hey Knock It Off,” build up to “Big Talk.”

A “Hey knock it off” approach means speaking up in the moment to check him when he crosses your line. Practice saying a few different phrases. The key is to say whatever you are going to say in a neutral, no-big-deal tone, like you expect that the other person will listen to you and that things will be cool if they do. You’ll let him save face, you won’t hold a grudge, but in the moment?  He’s got to knock it off.

If he mis-genders you, correct him. “My pronoun is ‘he’, thanks!

If he touches you in a way you don’t like, extract yourself. “Sorry, can’t hug now.” Physically take his hands off you, move away, don’t sit next to him, etc.

If he tells people you guys are still together, say “Really? You broke up with me. Why do you keep telling everyone that?

You say in your letter that he’s holding onto some of your stuff. You may get it back eventually, but right now, let that stuff go completely. Assume you will never see it again. Otherwise it’s just one more thing keeping you connected to him in a way that you don’t want to be connected.

On every other issue, correct him every time he crosses your line. You see why you will be leaving parties on the early side from now on? It’s exhausting, right? But don’t be afraid to be prickly and bossy about your own boundaries. He is the one in the wrong.

Other people will notice what’s up and may ask you about it. They may try to argue his case or defend your ex, because maybe they don’t know the whole story, or because in the moment you are the one looking like a jerk to someone who is “just trying to be nice,” but they may also have your back.  Don’t assume!  But be secure in knowing that you haven’t done anything wrong, and you don’t owe it to your friend group to never ever have conflict. You get to stand up for yourself and risk making it a little bit weird for your own safety. What you say to them is some variation of “You know I love (ex), but he’s been crossing my boundaries since we broke up, and I need him to knock it off. Thanks for understanding.”

There’s a lot more info about how to handle group dynamics/busybodies here. If at any point you feel actually unsafe, get yourself the hell out of there and be as awkward as you need to be. Group harmony be damned!

Step 4: Give it some time. It may take a little while and a few tries for your ex and your friends to get the message that some things are not okay. You don’t have to put up with anything that you don’t want to, but if you can frame it for yourself as a choice and decide that you can ride it out for a month, maybe you won’t have to scorch the earth.

Maybe the time will come when you have another Big Talk with your ex about your boundaries and ask him why he is acting this way. I would try some “Hey, knock it off” enforcement for a few weeks before that so you have some documentation that there is a problem or give him a chance to figure out that he’s not going to get the attention from you that he wants. Maybe you can have a buddy sit in on that talk with you to hold your hand and have your back. In that talk, you say “Hey, ex, you are making me so uncomfortable. And you’re making me afraid that if I speak up, I will alienate all these friends who are so important to me. Why are you doing that? Can we figure out a way to be around each other where we both feel ok and can be close and care about each other?

If after a month he’s still behaving this way? And your friends aren’t backing you? Then you’ve got to go. But if you feel you can give it a little bit of time in order to save the friendship(s), I won’t give you shit for putting in that time.

Step 5: Branch out. Make an effort to meet some more people so that your friend world is not caught up completely with these people. I’m sorry, it would be so unfair if you had to bail on this group because this guy is acting like a jerk, and hopefully the steps above give you every chance to make things right, but you will be taking care of yourself if you expand your network.

Step 6:  Practice excellent self-care. Body and soul. Get enough sleep, food, exercise, reading for pleasure, dance parties – whatever makes you feel nourished and whole, put the time into it.

I hope these friendships can be saved for your sake and for theirs – they’d be missing out if they lost you.


It’s still Pledge Drive week, with 3 days down, 4 to go. Thanks to those who have contributed already, it makes a big difference in my life.



13 thoughts on “Question # 164: Redrawing boundaries with a possessive ex.

  1. This is really, really good advice that sounds like it would be really hard to follow. I think the most important parts Step 1 and Step 5, because that might make the other Steps a little bit easier. That doesn’t mean they’ll be easy, but if you feel like you can’t do it, know that you probably can.

    Also, if making other friends and telling your ex to knock it off end up changing your relationship with this group (to the point where you aren’t really a part of it anymore), that’s okay too. You don’t need to be friends with people if the friendship isn’t working, even if you still really like them.

    1. The option to bail always, always exists, but you’re not obligated to pull the ripcord right away. Is bailing and finding new friends easier or harder than having a few difficult conversations?

      1. Totally agree. I would not suggest bailing right away (unless the situation is dangerous, as some down below suggest it might be, but even then bailing might not be easy/possible). I just meant that if the LW feels he’s becoming less close with this group as a result of standing up to this guy and making other friends, he shouldn’t feel obligated to try to stay close.

    2. I hear ya, Copcher, and I tend to read all advice with a boulder-sized grain of salt inscribed with the following phrase:

      Simple is not the same as easy.

      One does not simply walk into Mordor, unless you’re a hobbit and that is exactly the kind of thing you do, and it works.

  2. This is very good advice, assuming that your ex is actually a safe person to be around.

    However, based on some of what’s going on, I want to quickly advocate keeping that good ol’ Gift of Fear advice in the back of your head in case it’s needed. If your ex starts escalating his behavior in response to your de-escalating strategies, bail. Quick.

    1. I second this. Reading this letter gave me the “no”-feeling in a big way. Be safe, LW, and if he does escalate things, document everything.

  3. So sorry to hear this, LW. I am a trans dude who made a Big Move to a new city fairly recently; it’s tough enough to find a new social group without some douchebag (I don’t care what other good qualities this guy might have or how nice parts of the relationship were, this is capital-D Douchebag Behavior) mispronouning you.

    I’m pretty creeped out by the idea of this person breaking up with you, being actively disrespectful in what language he uses for you, AND also claiming to still be dating you. Those things are so weird together that it makes my mind jump directly to “potential personal safety risk.”

    One thing I’ve noticed is that even compared to other self-assertive behaviors (which I tend to find difficult), pronoun correction is one of the hardest things for me to do. It’s less of an issue for me at this point, but early in my transition when I was around friends who’d already known me for four or five years before I asked them to use different language for me, I’d go out prepared to correct people but would just deflate the moment I heard the wrong pronouns come out. I’d pump myself up before parties: “you know Phil will fuck up, so be ready the moment he opens his mouth to jump in and correct him” but Phil would casually spew some shes out and I’d flinch like someone hit me but not be able to say anything in the moment. I’m pretty good at correcting other people’s pronouns when it comes up but my own are always a challenge.
    It was very easy to make the leap from “people who say they care about me aren’t using the right language in the moment no matter how ok they said they were when I came out” to “I’m doing something wrong in my gender presentation/performance; I need to fix that before I can deserve the language I want.”

    I completely agree with the Captain that this correction is really important to do when the ex (or anyone else!) messes up, but I just wanted throw it out there this I find this incredibly difficult; if you do too, LW, you’re not alone.

  4. LW, your letter said that you “recently moved” and met this guy/this group of friends. I don’t know what exactly that means in terms of time frame — recently moved might be a month or a year — but if it’s on the shorter end, I think there’s a stronger case for cutting off this guy and maybe exiting this group.

    Making new friends is hard and scary, and I imagine doubly so when you’re at the early stages of transitioning and found people who are supportive, but this guy does not sound like a positive force in your life or like someone who is likely to change his asshole behavior. You say this is out of character for him, but again — how long have you known him? Was the breakup the first real disagreement you two had? There are a lot of people out there who are lovely at first but as soon as conflict arises turn into real jerks. That jerkiness isn’t an accident, it’s part of who they are. You might be able to correct or at least mitigate it, if you put in the time and effort, but if you’ve only known the guy for a few months is it really worth dealing with this abusive behavior (and it is abusive, and frankly sounds kind of scary) over and over in the way the Captain suggested? I think her advice is excellent if you do want to stick it out, but I tend toward the view that you have better things to do than guarding yourself against this guy and correcting his bad behavior.

    If you can identify some of the people in the group who you think will hang out solo for a bit and will understand and support you when you tell them what’s been happening, that’s awesome and you should definitely go for it. But if you don’t really know them all that well, aside from the abusive guy, then it may be a lot easier and less painful to find some equally awesome people who don’t come with a jerk like that.

  5. What this sounds like to me, an outsider reading a part of the story on the internet, is general abusive behavior in the “gaslighting” vein. It’s as though this guy is relying on your sense of him as a “good guy” and the group’s sense of him as such to excuse his assholish behavior; assuming you will hold on to the idea of him as a “good guy” and not trust the asshole in front of you. I think there’s a part of being human that does not want to believe people we once liked and trusted were not what we thought. Frankly, I think a part of me dies a bit inside every time this happens to me.

    I admit to the possibility that this is situational assholery. But that doesn’t excuse it. If the LW chooses to continue being part of this social group, I think that plot point #3 is extremely important. Swift, unemotional correction of every misstep and intrusion is important, as will be maintaining that boundary if questioned by other members of the group. This is not acceptable behavior, and you don’t need to be part of a group that accepts it.

    Either way, I hope you find some true friends, either within or outside of this group, and soon.

  6. I agree with all the commenters who are concerned that the ex may be an abuser, based on the gaslighting (telling people you are still dating when he broke up with you) and (very disturbing and aggressive and dehumanizing behavior) misgendering. Accordingly, I would put a *lot* more effort into finding a new circle of friends, or, even better, more than one new circle of friends. It is much healthier and rewarding to have various friends in different contexts than it is to hang out with a single unified “gang”.

  7. You guys are all right on that the ex is sending up red flags – mispronouning, claiming they are still dating, holding onto the stuff are all power play behaviors. Bailing – COMPLETELY BAILING – is always an option, and the second the LW feels unsafe or unsupported he should absolutely do that.

    What I gave is not a “no, stay!” argument, it’s a “if you want to stay and try to make it better, here are some steps that may or may not work” argument.

    The reason I say this is that there is a person in my wider friend group who has done some bad shit to someone else in my wider friend group. I did not like the Bad Shit person, and they always gave me a bad vibe, so I could run into them at a party and say a curt “Hey, how you been?” and then go talk to people I actually liked (also, no hugging. NO HUGGING EVAR!), but I did not know about the really bad shit. Their victim did not fully disclose the bad shit until fairly recently (like 5-7 years after I’ve peripherally known all these people). The victim of the bad shit was afraid that if they disclosed it, their friends would side with Bad Shit person or accuse them of making it weird and then all this stuff would be out there in the friend group.

    One side of this story is that the friend group has been coddling this bad shit person all this time, so the victim of the behavior should have bailed on all of us, right? Why engage? This group is made up of geeks, and has some of the attendant GSFs of “Ostracism is evil” and this guy still shows up regularly at parties.

    On the other hand, why should this person have to lose all their friends just because someone decided to act like an asshole? Especially when the friends did not know (and most DO not know) about the bad shit? Why not take a few minutes, have a difficult conversation with people you trust to be on your side, and give people the chance to do the decent thing? I haven’t traveled to the city where that friend group lives in a while, but the second I found out about the Bad Shit I preemptively blocked that person on all social media, and they are now a “They walk into a room, I walk out of it” person. If I see them even hint at any bad shit or even look at my friend crosswise, I will publicly shut them the fuck down and I don’t care what people think about it or if I made it weird. The victim of the bad shit is 100% my friend and I will 100% have their back in any conflict. Bad Shit person has earned my permanent side-eye.

    The LW’s story could play out many different ways, and trusting his instincts about what feels dangerous and abusive is paramount. Maybe they went from dating to being friends too soon without a distancing/cooling off period and some of the awkwardness is coming from that. Maybe the ex is having second thoughts about ending the relationship and it’s coming out in a shitty, horrible way, and he needs to be shut down right quick.

    When I was new at setting boundaries I was terrified that if I said no or got angry or yelled or said “hey, knock it off” that I would destroy my relationships – no relationship could withstand any conflict whatsoever, so I would bottle it all up and then bail because it was easier than saying stuff out loud. Now as an intermediate fence-builder, I’ve realized that most relationships don’t crumble the second you say “I love you, but you are acting like SUCH A DICK right now, can you please stop doing that?” (or the second someone says that to me, which has happened, and when it has happened it has been roundly deserved). We all know how to hide in our geek corners and not say any of our emotions, and we all know how to DTMFA, so in this answer I was experimenting with a middle way (which may not work).

    Thanks as always for making great points and having the LW’s best interest at heart.

    1. Yeah, this one is actually really similar to the letter with the sister who won’t stop calling the LW a slut, in my opinion. Both situations include a person who seems to be using an intimate relationship as a stage to act out some pretty ugly feelings. Or maybe to prove to themselves that they can do and say anything they want to, and still keep the LW’s friendship. I don’t know.

      I agree with you that people who are being victimized in this way, by a person close to them who suddenly decides to go balls-to-the-wall hurtful and ignore all kinds of boundaries, shouldn’t have to cede their entire friend group to one jerk. But yet, nobody is required to expose themselves to a person who’s acting like that. And further, nobody ought to be required to trot out a justification for not wanting to be Best Friends with the jerk, if they don’t feel comfortable disclosing sensitive information. It sounds like your friend was able to find a middle way, sticking with the shared group of friends, subtly avoiding the jerk, and only disclosing the full extent of the situation when they felt OK doing that.

      Awesome – and only possible due to your friend being an awesome person, and the Bad Shit person being a specific type of Bad Shit person. I’ve personally engaged in the sort of social engineering your friend did, too, and was pretty successful. HOWEVER, my warning above is based upon a second experience trying to manage an acquaintance who went all Bad Shit on me, and trying to use the same tactics I’ve used successfully before. That particular situation blew up in my face in a spectacular giant explosion that left me lacking yet another small portion of my basic faith in humanity.

      Honestly, it’s fine to decide you are going to be the bigger person, school an individual with abusive tendencies on how to cut it the fuck out, and refuse to cede your social circle to that person just because they are capable of fighting dirtier than you. There’s no reason to put ourselves into a false dilemma situation of keeping the jerk or losing the entire friend group, just because it appears too hard to articulate our needs.

      But only if the other person is actually the sort of jerk who sees “stop that” as a sign to STOP THAT rather than a sign that they’re getting to you and need to step it up a level.

      Let’s be clear on this, the ex might be teachable, he might know when to say “when”. In fact he probably does! But, there are people out there who just don’t. Who will escalate in ways that seem utterly remorseless. Who are really good at getting you into double binds and shitting all over the middle way no matter what tactics you try out.

      Recognizing those kinds of people before they get the chance to inevitably emotionally curbstomp you is a priceless survival skill.

      [One caveat to all this is that there are definitely friend groups who are capable of tossing out the jerk. But not all are. Some would rather enable the jerk than personally face their wrath]

      1. Ah, basically what I’m trying to say is that LW is only in control of his own actions. He can try things to deescalate the situation, and he can (and definitely should) articulate what’s going on to his other friends.

        But if his ex has decided, “I’m gonna go nuclear until I never have to see LW’s face again” then his ex will go nuclear. And if the friend group is overly ridden with Geek Social Fallacies, they will act out their GSFs.

        You can be your very best version of you, you can take the high road, be clear about your needs, sit people down for a heart-to-heart or two, and assert yourself. But in the end… still…

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