Dear Captain Awkward,

A couple of months ago, one of my best friends (we’ll call her Beth) and her partner (we’ll call him Dylan) broke up. Beth and Dylan had been together for six years and living together for five. They seemed to have a pretty good relationship, although Dylan dominated the apartment with his belongings, said he couldn’t marry her until he was a “real adult” (at 34, while doing nothing to move toward his definition of “adulthood”), and was generally kind of moody. Beth did most of the adult work in the relationship, including keeping a job she didn’t love in order to support them financially and doing all the emotional labor because Dylan wouldn’t go to counseling, individual or couples’.

They broke up because Dylan deleted their anniversary on Facebook. When Beth asked him about it, he confessed that he had been secretly dating a coworker and no longer loved Beth. She was blindsided, not least because she was very good at checking in on the relationship and he had essentially gaslit her into believing that everything was fine for months. Dylan moved out of their apartment and Beth actually packed his boxes for him. I did everything I could to support her and tried very hard not to set Dylan’s things on fire and to discuss my deep contempt for him with mutual friends instead of with Beth. Eventually it came out that the coworker was married and she created a lot of drama and misery for Dylan, and I thought, Great! He’s getting his and I don’t have to do anything.

Unfortunately, now that his little fantasy didn’t work out, Dylan has decided that he DOES love Beth after all, and he is insinuating himself back into her life and her apartment. She told me yesterday that they were having sex, but that he “can’t make any promises right now” and he says, “We shouldn’t be doing this” (while still managing to fuck her), which is basically the sexiest thing someone can say. Beth, heartbroken and holding out hope that he’ll come back to her and they can make it work, isn’t doing anything that I haven’t done myself, but I am furious that Dylan is taking advantage of her feelings so he can have AND eat ALL THE CAKE. But of course when I tell Beth that, I become the Bad Guy. Captain Awkward, I don’t know how to support my friend while also making it clear that there’s no fucking way this guy is getting back in our good graces, especially not with this behavior.

Thank you for your time!

Hard-Hearted Harpy Wants Friend to Be Happy (she/her pronouns)

Hi there.

When friends are in sketchy & manipulative relationships we’re so scared of being honest and maybe pissing our friends off, because we know that the manipulative sketchy person will use that as a wedge to drive us apart and isolate their prey further. We don’t want to act like smug assholes who are smarter than our friends about their own relationships. We don’t want to give the manipulative partners ammunition to say “Well your friends have never understood our perfect love,” so we stay gentle and ask questions and let them take the lead. This is generally a good quality and a good practice? But it has its limits, like when you feel like your own integrity will snap in half if you don’t say something. And part of being a friend is telling the truth.

You don’t have to pretend to be happy about The Return of Dylan. You really don’t. Next time Beth wants to talk about Dylan, you can say:

“Beth, you’re the boss of you, and if having some ex sex makes you feel better right now….okay? You get to work out your feelings at your own pace and lots of people have had bad-idea-sex with their exes. I don’t judge. But I am NOT gonna pretend that I don’t think that dude is sketchy as hell and I am not going to be able to keep a straight face and say polite, non-committal things when you talk about getting back together with him. If you need to vent or figure this out while I roll my eyes and cross myself at every mention of his name until he’s out of your system for good, okay! I will will try! I want to be supportive, but I just can’t form my lips to say anything nice about him.”

She might go all tight-lipped, she might get it, she might decide to talk to you less about Dylan-stuff, I don’t know. When I was pining over a series of Darth Jackasses I sorely tried the patience of my dearest friends and it did help when they finally snapped and said “NO. STOP. AND IF YOU MENTION HIS TEXTS ONE MORE TIME, AM TAKING YOUR PHONE AWAY FOR THE REST OF TODAY. NO MORE.” and also a less shouty but no less true script, like “Listen, fuck who you want, you will anyway, but it is a beautiful day and you are not gonna ruin OUR PRECIOUS FRIEND TIME with talking about gross boys, knock it off.” Like, my sad longings and indecision and woe about people who had proven themselves unworthy in every possible way were not allowed to ruin every single brunch! That was good friending on their part. It helped me shake off the fog of manipulation.

So, maybe you say the thing once. You don’t have to harp on it, but you can stop biting your tongue. It’s gonna take her as long as it takes to be rid of him and that’s so very hard to watch, but you don’t have to pretend to be happy or even neutral about it.

You can also suggest Beth find a Dylan-neutral sounding board like a therapist (this neutrality is probably good for one session, then that therapist will also hate Dylan the way you & I hate Dylan, but they will also have training that you and I don’t in not rolling one’s eyes and screaming NO!). But it’s okay if sometimes you are like “Listen, I am trying my best here, but COME ON, REALLY, THE MOODY USELESS ASSHOLE WHO CAN’T EVEN CHEAT ON YOU WITHOUT MAKING A COMPLETE RUIN OF HIS LIFE, THAT’S WHO I’M SUPPOSED TO ROOT FOR? COME ON. NO.”

If she goes back to him, it’s not because you were “unsupportive.” Sometimes our hearts are real jerks and they let us down and assholes crawl in an set up shop there. You’re not the boss of Beth but you’re also not responsible for what Dylan is doing here. You’re a person, too, and you’re not a bad friend if you can’t maintain eternal therapist-like distance when someone is hurting your friend.

P.S. Here are some great visual aids that came into my life today, at just the perfect time.