Should I Date my Friend who Has a Boyfriend?

Visitor's Question from a 21-30 year old Male
I have really liked my friend since I met her. Our relationship as "friends" developed to the point that I am now her best friend. We go eat, go to events together and other stuff.

She has been dating someone else for about a year now (I think it is around 10.5 months). We just went to an upscale party together and on the way back she confessed that she liked me from the minute that she saw me and that her feelings developed during our friendship. She didn't tell me that she wanted to go out but held out the possibility.

The guy she is dating has already proposed to her and she told him it was too soon; that she wasn't ready. Lately she seems disinterested in him. On the car ride back she told me she wanted to go to a play and intimated that I should get tickets (although she didn't directly say it). Does this mean that she likes me and is telling me to ask her out on a real date?

I really don't want to mess up the relationship with her current boyfriend, although I don't think he is a good influence on her (he is very "grungy" looking and gets into fights all the time). I also don't want to mess our friendship up. Should I take her to the play and to dinner and talk about it or just leave it totally alone? I'm pulling my hair out. Help???!!! Advice
You're definitely correct to be worried here. This has all the markings of certain disaster. The key thing is that this girl is having trouble making decisions. She has a guy she is dating and is at the point of marriage with - but she's having the normal butterflies that just about every about-to-marry person has. Instead of dealing with those concerns and making a decision, she is playing the "safety net" game. She has you on the side, and is working to see just how much she likes you, if she should really stay with the first guy or if she should ditch him and see you instead.

No matter WHAT you do, she is going to blame you if things go wrong. Let's say she decides to stay with her guy. You will always be a reminder that she was cheating on him when she should have been working on the relationship with him, and it will destroy your friendship. Let's say she decides to ditch her guy and go with you. Now any time you have even the slightest issue (and all relationships have their ups and downs) she is going to bring up that she COULD have been happily married to her ex, but noooooooooo you had to drag her away, force her to leave him and NOW look where she is.

THE most important thing for any human being to do is to honor her promises, deal fairly with people and be honest. If you assist her to be a cheater, she will always remember that even though it's her own fault that she pushed you into it.

Friends go to plays and dinner all the time. So what I would do is take her to the play and dinner as a friend. But make it clear to her that SHE must decide what SHE wants to do here. That you can't become her 'back door man' - that it isn't worthy of the important friendship that you have with her. That she can choose to stay with her fiance-to-be, and you will support her in that! Or she can choose to break up with her fiance-to-be, and you would support her in that as well. But SHE must choose, and SHE must choose that soon instead of being disloyal both to her current guy and to the friendship she has with you.

I think if she knows you will be there for her as a friend, no matter what, that she might find the strength she needs. But she's treating this almost as a game right now, which is completely unfair to everyone. She has to start realizing that being in a relationship is a serious commitment that involves peoples' lives and life-long dreams. If she isn't 100% working on her relationship with her fiance, he deserves to be TOLD this and allowed to go find a woman who IS. This guy wants a house, a family, children and a long term life. Instead he has a girl who is stringing him along while she considers other guys. That's very unfair to him, even if he is a bit grungy.

-- from Jenn
One of Your Friendly Advisors at

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