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The Hook Up: How to break up with minimal collateral damage

Hey Anna,

I’m 17 and identified as gay until some months ago, when I met an awesome guy. I came out to him as bisexual a few weeks after we started dating and told him I previously identified as gay. He is totally fine with that, which is just one of the reasons he’s a generally on-point considerate boyfriend.

However, he didn’t get me 100% over my previous (female) crush-90% max. Around when I came out to him, she came out to me as also bi. Either because of that, or because I just can’t keep my heart under control, I’m now 0% over her. She also has a boyfriend, since before we discovered our common queerness. Nothing’s going to happen between us in the foreseeable future, but her hold on me seems relevant.

Due to her and other less clear reasons, I’m really not feeling it with him. I think he’s amazing and we get along well, but something’s missing. I was happy to identify as bisexual for a couple months, but am now re-evaluating that. I won’t give details (vagina gay, heart less picky-to paraphrase your articulate self), but for a while at least, I was genuinely into him. We’re 95% over, but I’m not sure he knows.

We don’t see each other much, but he wants to talk in person. He said this was to try to make our relationship work, then that is was just to talk it over. I told him we could, but I hate emotionally wrought conversations in person, and I don’t know if it’s wise to meet him face-to-face if we could get into a serious argument. Although slightly worried about my actual safety, I’m more afraid that one (or both) of us will cry and I won’t know how to deal, or I’ll say something dumb when put on the spot. I’d rather explain myself in an email or something. Is that an okay idea? Should we meet up? Should I tell him I think we should end it before, during, or after that? How can I leave with minimal damage to him and without being a stereotypical manipulative/confused/unfaithful/indecisive bisexual?-Stuck

Dear Stuck,

Do you remember that scene in season 4 of The L Word when Alice breaks up with Phyllis, but Phyllis doesn’t quite want it to be over, and Bette tells Alice “Some lesbians you have to break up with more than once”? (It’s here, around the 4:40 mark if you don’t). Well, some straight dudes you have to break up with more than once too, Stuck. Though, in truth, I’m not quite sure you broke up with him once either. Except this line is telling: “We’re 95% over, but I’m not sure he knows.” You should definitely say actual words to him to the effect of “I don’t want to date you anymore.” Have you? If you have not, I suggest you get on that. And it should be in person.

I know, breakups are the worst. Confrontation is the worst. Emotionally wrought conversations are the worstest worst, but they are a necessary part of an evolved life, and of being a considerate, well-rounded, empathetic human being, which I know you are, as evidenced by your articulate, thoughtful letter. It is precisely these kinds of icky conversations and losses that make us ultimately thrive, Stuck. That we survive them is a testament to our aliveness and our willingness to grapple with ugly truths. I know you’re 17 and therefore near the beginning of your long and prosperous and tumultuous and glorious romantic existence, but even though you don’t like the idea of doing this in person, you’re going to have to do it, probably multiple times, as you get older. It sounds strange to view a breakup as “practice,” but, well, the only way to get better at something is to actually do it.

So do it. Break up with your generally on-point, considerate boyfriend. Do it even though it’s hard and you won’t know what to say and you both might cry (it’s very possible). Do it swiftly and as compassionately as possible. You don’t have to know all the answers to questions he might ask. But you owe it to him and to yourself to make a clean break of it so he can move on and you can move on and neither of you will be left in this sorta-kinda relationship purgatory.

A few additional breakup tips:

  1. Don’t expect it to be easy or quick. Leave yourself enough time to hash it out and recover from any crying jags before you have to be around other people again.
  2. Do it at the dumpee’s house. That way, you can cry all you want, leave when you want, and he will be in a place of familiarity and comfort. Some people suggest neutral territory, like a park, and if you are concerned he might cause a huge scene or do something scary, this is an option. One of my life rules, however, is to cry in public as little as possible, so I prefer houses.
  3. If it helps you, prepare a short speech beforehand. At the very least, clarify your feelings so that you have an idea of what to say and your reasons for ending things. Bullet points help, in my experience.
  4. Be honest, but not soul-crushingly so. For instance, “My feelings for you have changed” is better than “I can’t stand your penis.” Be gentle but firm.
  5. Don’t make any promises or lead him to believe in the future your feelings for him will change.
  6. If possible, have an escape plan after a certain amount of time has passed, e.g. “I have to pick up my friend from soccer practice.” This helps to ensure it won’t drag on endlessly and result in a lot of terrible Feelings Poetry.
  7. And don’t make plans to hang out with him anytime soon. Though you can say you’d like to be friends again someday if that is something you want. Just not tomorrow.

You can get yourself unstuck, Stuck. On that point I am 100% certain.

I am a 28-year-old bi girl. I got into my first relationship with a slightly older lesbian woman last year. She is really amazing and supportive and a great person. I feel more secure and happier than I have in any of my previous relationships. Two things always eat away at me though. One, although the sex is great, I don’t think she is objectively beautiful. I don’t look at her face and find it beautiful. If I’m being painfully honest, sometimes I find both her face and her body slightly unappealing. I know this is not the case the other way around. Also, I am concerned that because we got together right after I realized I had feelings for women, maybe I rushed into it a bit.

These feelings all came up during a three-month trip to South America. I felt like I was really interested in other women and when I was drunk I would have a strong desire to kiss someone else. However, this didn’t happen until the last night. I met a girl who I felt a really intense connection with and we hung out exclusively for three days. She was recently discovered bi too and it was great to share my experiences with someone who could really understand. On our last night together we finally made out, and I think it would have gone further if she didn’t have to rush to her plane. I told her about my girlfriend but made it sound more casual than it was.

I found this girl interesting and beautiful and had a connection that I really haven’t felt before. Now I have two weeks traveling with my lovely, supportive, and wonderful girlfriend, but all I can think about is this other girl. I have tried to tell the other girl her how I feel, subtly, but she is being really reticent. I don’t know whether to trust my experience and instinct (because it really felt like she felt it too) and to keep on going, try to visit her when I’m back (we live in different countries in Europe), or whether to leave it, to get the hint, and respect my girlfriend. I want this girl to be straightforward about her feelings for me, even if they’re nonexistent, because that will help me move on. Now I just feel like I’m in a limbo where I can’t think of anything else but this girl, when I know I should be focusing on my girlfriend and the danger of destroying our relationship. I just feel so melancholy and hopeless and I’m going mad. I don’t know if there’s any advice for this apart from “get over it,” but any ideas would be great.-Confused and Sad

Dear Confused and Sad,

Vacation girlfriends are always so romantic, aren’t they? There you both are, away from work or school obligations, in a tropical paradise, footloose and fancy-free, and every minute spent together feels momentous because it is fleeting, and you know your time must come to an end. Who wouldn’t fall in love in those conditions?

Before we talk about “getting over” this dreamy vacation girl, let’s discuss the giant elephant in the advice room, Confused, which is why you haven’t broken up with your current girlfriend whom you quite obviously do not want to be with anymore. Can we talk about that, sugar shoes?

Please break up with your lovely, supportive, and wonderful girlfriend whom you are not attracted to. I know that doing so may feel shallow and unbecoming and hurtful, but I also know that your thinking, fantasizing, and actually making out plus more if she didn’t have a plane to catch with other ladies is a larger, more compelling voice than the one asking you to stay with someone you don’t want to be with. Listen to it.

Of course you feel melancholy and hopeless and like you’re going mad, Confused. Anyone in your situation would be. You are actively lying to and betraying someone you care about. You are wrestling in the murky lust-waters of uncertainty with the spectre of a girl you barely know, all while pretending everything is hunky-dory with your partner. And so, before you even begin to think about building a future (or more practically, a first date) with this new girl (or anyone), you have to hunker down and have a serious, truthful, heart-rending conversation with your girlfriend and with yourself, and end things. Ultimately, dreamy vacation girl doesn’t even matter. What does matter is your integrity. What does is living a life of honesty and profound vulnerability and respecting your partner enough to let her go.

I suggest you grapple with the questions that are right in front of your nose. Let your past actions be an impetus for transformation. You are steering the car, Confused. You have the power to drive yourself un-crazy. Will you? Will you allow this less-than-ideal situation to alter you, or will you throw up your hands and keep grasping at convenient untruths?

Also, for what it’s worth, it’s pretty rare for dreamy vacation girls to turn into dreamy long-term partner girls, especially those who live in other countries. This isn’t to say it’s impossible, just that your experience with her might be bound up in the brief, glorious haze of South American splendor. Your connection may have felt real and strong and powerful, but it also might not translate to the everyday soul-suck of reality. Possibility is a mighty drug. It is best taken in small doses.

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a writer living in San Francisco. Find her at annapulley.com and on Twitter @annapulley. Send her your The Hook Up questions at [email protected].

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