Ask MR: My Friend Always Dates the Wrong Guys — And Wants My Input

Hello and welcome to our advice column, “Ask MR,” where we answer your burning questions in the hopes of being the ointment to your life rash. Ask us questions by emailing with the subject line “ASK MR A QUESTION,” or leave yours in the comments.

Hi Man Repeller,

My friend ALWAYS dates the wrong guys. By wrong I mean unavailable — clearly so — or have addiction problems, or won’t ever commit, or don’t live in this city. She also ALWAYS asks me what she should do when things go wrong between them, or for advice when she’s worried things are about to end. (“Should I post this Instagram to make him jealous? What should I caption it?”)

I have basically stopped trying to help her. It’s frustrating to have to be the one she seeks advice from during the process, even though she never listens, and then to be the one she cries to afterward.

It’s just exhausting. It’s like Groundhog Day. What do I do?

Okay. I know this friend. I know that to be a friend to this friend is, as you said, exhausting — mentally, emotionally, sometimes physically. (I have been roped into some strange, late-night Dedicated Wing Woman scenarios where I’d rather be in bed, or eating, and yet it’s 3 a.m. and I’m nursing a stupid beer on a stranger’s couch for That Friend’s sake.)

I know how annoying it is to repeat the same advice and watch as it flies in one ear and leaks out the other, to listen to the same stories on a loop, to fake-smile in a way that communicates “I am tolerating you, I do not like you” as you shake the hand of her new bad idea. I know how truly distressing some of the scenarios this friend gets involved in can be, how they can open your own old wounds and how the toxic runoff of this friend’s relationships can — when you are this involved — affect your friendship and your life.

I have also been this friend before, to some extent. I have dated the wrong guys and then ignored everyone around me who offered logical advice like, “Get out now.” I have explicitly sought advice and then, not getting the answer I wanted to hear, threw good council away. I have been plain dumb. What ended up happening every single time is that I learned a new lesson the hard way. Sometimes, no matter how many ominous predictions you’re given, no matter how many cautionary tales you’re told, no matter how many words of wisdom a patient friend strings together for you over various dinners and late-night phone calls and screen-shot-analyzation sessions, you are going to do exactly what you want to do and then deal with the mess later.

When you are the friend being given advice, it is very easy to feel judged, patronized, like a child, like an idiot, like a shitty person. Even when you asked for the advice. But I think, worse than that, is to feel like you have no one to talk to. You said your friend has repeatedly sought you out, so first take comfort in knowing that at the very least, whatever you say to her offers her some sort of solace. You do not make her feel judged or patronized. I would bet that the advice you’ve given her floats closer to her conscience than you realize, that your words are not tossed on the floor with as much carelessness as you may think. She trusts you.

If you are her friend and she is yours — that is, if you want to keep this person in your life no matter how much of a tornado she brings with her — there are two options. One serves her better, one serves you better.

The one that serves you better is to tell her (aren’t straightforward conversations just the most fun and so comfortable??) that you feel unqualified to help with these kinds of problems. That you feel you’re actually doing her a disservice by offering input. You have every right to say, “I love you very much. I care about you an enormous amount. I want the best for you. I want to discuss politics and TV shows and oceans and weird Google-searches and French fry preferences with you until we lose our voices. I want us to develop a whole new language so that we can talk about our deepest secrets and scariest thoughts with one another in public. I want us to get shushed because we can’t shut up! I will always be here for you, but I can’t council you on dating stuff anymore. I think these are decisions that are best left to your own making.”

She might think that’s kind of selfish of you. She might get mad at you for a while and feel abandoned. Know that if you say this and if she agrees, you revoke your “rights” to offer future unsolicited relationship opinions and advice. She may be wary to introduce you to any new partners, including the good ones, because she may think you’re jealous. Or that you don’t want to hear about it. I’m being a little dramatic on her behalf, but if you’re her one person she tells all of this stuff to, then she might feel thoroughly lost. If you are true friends to one another, though, ultimately, she will respect your decision even if she doesn’t “get it.”

Option two is that you remain her one-woman board of advisors and accept your role as therapist. If she dates the men you say she does, then she needs a true friend to help her through it. She needs a true friend to celebrate the victories and reinforce the healthy relationships. But! You can still set up boundaries so that you remain in your comfort zone. For example: “If he’s married, I don’t want to hear about him. My answer will always be the same.” “My friendship services to do not include Instagram consulting.” You can set up time limits: “Let’s talk about relationships for half an hour and then switch to sports or literally anything else.” “I don’t answer my phone for anyone except Oprah after 2 a.m.” Again, it may sting her (imagine being clocked while venting…), but if she respects you, she will respect your wishes.

It’s up to you to decide which option to go with. I can’t tell you what’s “best” for your individual friendship. In fact, you may listen to none of this! Because as we all know, advice — when sought out — is nice to read, to hear. It’s comforting. But it doesn’t mean we’re going to take it. Still, the good stuff stays with us, somewhere in our heads, so that when we really need it, we reach for it. Right where we left it.

Last month on Ask MR: Am I annoying? 

Collage by Maria Jia Ling Pitt; painting by Mary Cassatt, photo by Barney Burstein/Corbis/VCG via Getty Image. 

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