I like her, she likes me, but she’s got a boyfriend. How do I win?


Zippetybop asks:
I [28M] want to give an ultimatum to her [26F]. We are both in business school. During the first week, she met this guy that treats her like a princess, and they have been together for over a year now. Her and I became very close and at one point when they were broken up, we made out. It all poured out to each other about how we get along so great and how we wish we met each other earlier. We were inseparable. When they got back together, she had some sort of guilt trip and we slowly stopped talking.

Not sure what happened or if she is getting bored with him again, but we are hanging out again. I have strong feelings for her, and I don’t care about her boyfriend. If I could have her, I would be so happy. She really loves attention, and sometimes I can’t help but give it to her because I love hanging out with her. What is the textbook answer on what I am supposed to do in this situation. I’m more than willing to play the game, lol. She loves me and is practically guilted staying with him, hence her hanging out with me so much.

How do I win!?

Demetrius says:

As with many things in life, even when you win, sometimes it’s a loss. And sometimes, losing is the best thing that can happen to you.

I guess my question first would be, what’s your goal. If you’ve got a goal in mind, “winning” is a bit more achievable because it helps you plan the steps you’ll take to get to that goal. If your goal was to have the most points compared to a team you’re competing against, your steps to win would be simple. Prevent the other team from scoring more points than you, or score more points than the other team. But, what’s your ideal situation here? She decides that it’s time to breakup with her boyfriend, breaks up with him, and then enters into a relationship with you? Is that the end goal you want?

If that’s the goal you want, an ultimatum is your best move. It can be as simple as asking what she plans to do and whether or not she sees you two ending up together. Alternatively, you can just set a hard ultimatum like “leave him in 30 days or we’re done”. It seems like if she’s ever going to leave him, she’s going to need a push. The best way to force someone’s hand, when you have the upper-hand, is to give them an ultimatum. Assuming that she’d rather be with you than with him, you might have to leverage that if you feel like she’s dragging her feet on making a decision.

You do risk losing her completely by giving her an ultimatum though. An ultimatum is a gamble in almost any situation, and people respond in interesting ways once you put a little pressure on them. Maybe she’ll decide that the time she’s invested into her relationship has not been properly rewarded yet, so she’ll devote more time to the relationship leaving you holding your hat. Or she could decide that maybe you and her current boyfriend are making her perpetuate some very bad dating habits, she’ll decide it’s better to just drop you both, and you’ll never hear from her again. Or she could just stall for time, as many people would when they’re getting their cake and eating it too. Either way, it’s very possible that an ultimatum pushes her away, rather than pushing her to make a decision. Ultimatums always carry the risk that they’ll choose option B, always remember that.

Here’s the thing I hinted at earlier though: If you win this girl, you’ll also be taking a huge loss. I’m sure she’s lovely and all, and maybe she makes you feel the way Tormund Giantsbane feels about Brienne of Tarth, but strip away all the niceties and here’s what you’ve got. She is a woman who likes to be coddled in relationships  i.e. being treated “like a princess”, requiring a lot of attention and affection, etc. She’s dating a guy who gives her exactly that, they were briefly on a break and she sought out that same comfort from a friend who is very much into her, which she could probably guess just by looking at you. They get back together after you gave her the attention and affection she craved on her break, but now she still seeks that attention from you, and her boyfriend who she has not left. I’m sorry but, do you really want to date that person? If she leaves him and gets with you, the first time you have an argument odds are exceptionally good that she’ll seek out the same attention and affection you were giving her as her vaguely platonic romantic interest from some new guy. Do you think that you make her feel special, or that she seeks out the feeling of feeling special?

In case you were wondering, why yes I have been in this exact same situation in the past, how did you guess? Long story short, we met while she was on a break from her boyfriend, we hooked up, they got back together, we continued to hook up, they finally broke up, we start dating, she left me for some other guy who she later married, then divorced. She was very much the “want to be your focus/I need a lot of affection” type of person, or at least I remember her that way. People who seek out the comfort of relationships, while in relationships, are rarely looking for a specific person, they’re looking for a feeling. Appreciated, loved, desired, what have you. Y’know how the common adage is that men cheat for the physical, and women cheat for the emotional? Well it’s not always true in a gendered sense, but people tend to stray for those two reasons: Sex or Validation. I think in your case, the lady in question likes to be treated in a way that makes her feel like she’s the center of attention, and she’ll seek that out no matter who she is dating. There’s nothing wrong with requiring a lot of attention in relationships if that’s your thing, or wanting to be treated like a princess, but I think in her case, she’ll seek that attention out regardless of whether or not she’s in a relationship. It’s not like she’s known you for years and your attraction has built up over years of unrequited love and you’re the one that got away or something equally trite. She met you and her boyfriend around the same time, and somehow she’s managed to build a relationship, and a quasi-relationship with you, where she is treated like a princess. Do you think she’s likely to give that up to just be with you? Do you think that once she leaves her boyfriend, she wont seek out what you two had with someone else? I think she will if I’m being completely, so even if you did win, you’d still lose.

If you want to give her an ultimatum and try to win her over and try to prove my wrong, go for it. I’d cut my losses, only see her as a friend, if at all because I’m not seeing how you benefit in this relationship, and maybe pursue a woman who is available, and doesn’t need to be coddled. But that’s just me, maybe you like all this drama. ¯\_(ツ)_/¯

Good Luck Out There.

3 thoughts on “I like her, she likes me, but she’s got a boyfriend. How do I win?

  1. She’s clearly happy with the current situation. Think about it: She got back together with her boyfriend and still likes to hang out with this guy? Well she’s playing everyone! Take it from a girl: girls are annoyingly smart. She knows exactly what she is doing, and has everything she wants right now. Go find someone else to date, someone who doesn’t play games, someone who (if she really liked you) would give you a chance. MARY OUT.

    Liked by 1 person

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