Dear Polly,

I am on the verge of yet another destructive relationship and I’m worried that I’ll never know how to be in a healthy one.

Backstory: In college, I made it a point to sleep around as much as possible to try to “right” the fact that I was both invisible and undesirable in high school. In my group of relationship-oriented friends, I became a “lovable slut,” someone you don’t have a relationship with. I talked myself into this persona and then encouraged my friends to see me that way. I made a lot of dangerous choices and was very lucky to be physically unscathed and disease-free the whole way. When I finally was in a long-term relationship after college, it was toxic from the start, but my need to convince my friends I was now “reformed” was part of why I stuck with it. After it ended this year, I focused on getting in shape and getting career-oriented. I felt great, and I was even okay with not sleeping around for the first time in years — I finally stopped chasing the dragon. That was until last week when an old flame contacted me.

I’ve known “Ben” since college; we met at an annual party. We hit it off right away, and all signs pointed to us taking things to the next level. We decided to go someplace quiet, but as I was off getting my coat, Ben’s best friend “Mike” intercepted and asked me to leave with him instead. Mike was someone I had crushed on earlier in my life, and his advances were thrilling. Without saying good-bye to Ben, we left together immediately. Mike and I never spoke again after that night, but Ben and I remained in the same circles. I slept with many of the people in the group (when they were single!), and I eventually got around to sleeping with Ben. Ben treated this without emotion, so I pretended to do so as well (like a good slut should!) but was secretly falling in love with him. Though I’d apologized up and down, Ben used my feelings against me by saying things like, “Well, we could have been serious, but you … ” — fill in the blank here with a betrayal (real or perceived). Every now and then, Ben would throw me an emotional bone but was generally cold toward me. Two years ago, I decided that this emotional blackmail was too much and I cut Ben off by blocking his number and FB. I spent time overseas and thought about Ben very rarely.

So when Ben called me last week from a new phone and basically negged me into seeing him, I was shocked. I tried to say no, but when he told me he was down the block from where I was, I couldn’t stop myself. I left work early, in the midst of a project I needed to finish, and what followed was a very exciting, fulfilling afternoon. We talked a bit. He, right on cue, brought up “the Mike thing.” I know he’s thought about me a lot over the years. He mentioned details about me that lead me to think he checks my social media through a mutual friend’s account. I should be put off, but I’m thrilled.

Now I’m heartsick over him again. All the good work I had been doing to better myself has disappeared in the space of a couple of days. Normally, I’d put another notch in the post and try to forget. But he’s moved to my city recently and we are both due to attend the annual party we originally met at. Not going to the party will raise red flags within the group, but he’ll be there with his girlfriend. I can’t stop thinking about him and another encounter. I want him all the time even though I know he won’t leave her (“then I’d have to move again”). How can I turn my feelings off? Why is he still stuck on what happened in college all these years later? The last relationship I was in was emotionally abusive, and now I’m pretty sure I can only deal in dysfunction. This is past just being attracted to jerks. How do I break this pattern once and for all?

Side Piece of Mind

Dear SPOM,

It’s not hard to see why Ben was fixated on you in college. You showed interest in him and then impulsively left with another guy instead. If you were in his shoes and he disappeared without saying good-bye and you were wandering around asking other people where he went and eventually one of them told you, “Sorry, but I think he left with Vanessa ten minutes ago,” well, that would stay with you for a while, too. Maybe he really liked you. Who knows?

But since then, you two have slept together. He scratched that itch and made it clear that it wasn’t emotional for him. But that wasn’t enough. Somehow it didn’t erase the humiliation of you leaving with Mike. So now he’s willing to track you down and cheat on his girlfriend, just to have sex with you again and show himself that he can have you any time he wants to.

His motives now are crystal clear, and they aren’t remotely romantic. He wants to placate his ego. He woos you by insulting you. He isn’t looking for an emotional connection. He doesn’t want to hang out and talk and win you over. He has a girlfriend. Oh, and what are his reasons for staying with her? To avoid moving again. Haha.

This guy is bad news. The power you’ve wielded over him in the past still infuriates him, and he wants to give you an emotional noogie and rub your face into the carpet until you cry, “Uncle!” But even that won’t be enough. It’ll never quite make up for how rejected and weak he felt when you took off with Magic Mike. So not only is he tracking you down and revenge-fucking you now, all the while making it clear that he’s not remotely interested in you, but there’s a good chance that, in spite of his having a girlfriend, he’ll either try to get into your pants again or he’ll try to get you to demonstrate that you’d happily sleep with him again.

Your feelings for him will trick you into believing that this weird vengeful interest he has in making you feel embarrassed and ashamed of yourself might actually reflect his deep, passionate feelings for you, feelings he’s too tough to express. Wrong. His interest in you is not a compliment. It’s an insult. He wants to insult you to your face. He wants to put you in your place. He hates that you held sway over all his friends, and he was one of the last ones you deigned to sleep with, and he wants to take that power away from you, over and over again.

You’re not in love with this guy, trust me. You’re into him because you had sex with him recently, and because indifference strikes you as sexy. You like people who can play roles the way you can. You say your persona was “lovable slut,” but it was actually a little bit more cavalier and intriguing than that, whether you know it or not. You knew how to charm guys, and you also knew how to seem like someone who didn’t really care, who wasn’t about to fall in love out of the blue. That’s an adaptive posture for someone who’s hanging out with a big group and can see, very clearly, that women who care too much are often the butt of the joke. So you’re good at that Hey, Whatever, Let’s Have a Good Time cool-girl role, and you’re attracted to the male version of the same thing.

I know all too well how this works from personal experience. And it’s not an illogical approach to the overall dog-eat-dog sexism of college life. But know this: It doesn’t play well in the real world. Unpacking your jaunty seductress costume just to win this guy over would be an awful mistake, one that will set you back light-years and will yield zero emotional rewards. I get that it’s the easiest role to play: You’re good at it, it works, you get exactly what you want — at first, anyway. Being honest and admitting that you’re a fragile, thoughtful person whose feelings get hurt easily — that’s a far less winning formula, particularly among circles who knew you as a swaggery, take-no-prisoners type way back when.

For years after college, I fed my ego by acting like the swaggery boss lady of the party. But you know who likes that woman? Guys who think that feelings are for pussies. Guys who roll their eyes the second you tear up or say anything real. Guys who call women who actually care about the way they’re treated and stand up for themselves “psycho chicks.” Swaggery behavior attracts douchebags — flinchy douchebags, overgrown man-child douchebags, and ANGRY douchebags.

And look, when you pretend you’re a carefree cool girl but you’re really a very emotional, sensitive woman underneath it all, you’re essentially the female version of a pickup artist. You’re luring in your prey with an elaborate act. You’re feeding your ego. You wanted Mike because he finally wanted you. It was a notch, not a real connection. It’s a competition. It’s a way of feeling better about yourself, after feeling invisible in high school. “Everyone wants me,” you tell yourself the next morning, slightly hung-over, slightly demeaned by the cold tone your prey took as he said good-bye and exited your apartment.

Not only would I recommend against regressing into your lovable-slut role, but I’d recommend you work very hard to disassemble the many roles you play with this group of friends (and others). You talk so much in your letter about how your choices — to play the lovable slut, to seem “reformed” — were molded by your friends’ perceptions. What would it feel like to just show up without a script? How would it feel to tell the whole truth and nothing but the truth when someone asked you how you were? How would it feel to hint that you’re not on top of the world; that you’re not bulletproof; that you have feelings, and those feelings are important and they don’t necessarily make you a needy freak?

Once you recognize that people who are allergic to uncool are also allergic to feelings and vulnerability and magic, it’s pretty easy to avoid dysfunctional relationships and shake off guys who can’t handle real human beings with strong emotions. All you have to do is be honest. You just say, “I have a lot going on and I’m pretty intense right now, so I don’t want to spend time with anyone who doesn’t want to have serious conversations. I’m not really bullshitting around at this point in my life.” Maybe that sounds like a different kind of pickup line, a neg custom-designed to snag a sensitive guy (or a guy who wants to seem sensitive!). But that’s just an example. Your honest statement will be your own. The point is to push yourself to tell the truth instead of playing a role.

To be clear, I’m not talking about ways to win Ben over. You shouldn’t even talk to that guy. He’s made his motives clear, and even if he claims to want a platonic friendship with you because he really likes hanging out, he’s still just looking to administer that noogie. Trust me on that. The more you ignore him, the more he’ll sniff around wanting to prove that you still want him. This could drag on for decades, but not for any worthwhile reason. Don’t think of him as an old flame. Think of him as a recurring inflammation. His fixation on you is sick. It’s very likely driven by some deep rejection from his past. I know that sounds presumptuous, but this really doesn’t sound like attraction so much as ego compulsion and an attempt to right some big wrong that has nothing to do with you. Connections forged on such ground are by definition destructive.

You should find a good therapist and get some help figuring out the roots of your own role-playing compulsion. It’ll help in so many ways — most of all when you feel like you’re losing ground and you need someone to look you in the eyes and remind you of how far you’ve come.

For right now, though, listen to me: You HAVE come a long way. You don’t have to repeat old patterns. You’re not on the verge of anything if you don’t want to be. Remind yourself how lonely it feels to be with someone who doesn’t really want you. That’s who Ben is. He doesn’t really want you, and he’s a cheater on top of that. You want someone who wants YOU — all of you. You need to know that you can feel unsure and afraid and worried and upset and it doesn’t make you unattractive or unlovable. You want someone who’s strong enough and healthy enough to recognize that instead of making you feel like a freak for having feelings. You can start down the right path by being strong enough and healthy enough to recognize that for yourself.

You won’t believe how good it feels to go home after saying no to the wrong guy’s advances. You won’t believe how good it feels to know you’re going to treat yourself well and take care of yourself and keep yourself safe from stupid, half-assed situations that will only make you feel shitty. Once you do that, you won’t go back again — trust me.

Polly

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All letters to askpolly@nymag.com become the property of Ask Polly and New York Media LLC and will be edited for length, clarity, and grammatical correctness.