Advice, Please?
 

OK, this is a little personal (for me at least) but I want to ask people who are not close to the situation for an opinion.

At one time, about 4 years ago, my best friend of 20 years was engaged to a wonderful guy. She cheated on him, so he left. (I don't blame him) Since, she has been involved with a few others and is now engaged again. She has told me that cheating on him was the worst mistake she's made in her life, and it hurts to talk about him. OK. A few weeks ago, he called me just to BS, see how I was doing, and wanted me to go out and have a few to catch up. So, we did, this past weekend. We went to the boat, lost money, and had a blast. We're both interested in eachother, but I feel unbelieveably guilty. What do I do? What would you do??? The last thing I want to do is scar or even ruin a friendship of over 20 years because of this.

Her loss is your gain :shrug: I mean as long as you are above board about it - its her loss. She made that decision years ago :cool:

I guess I would ask her how she felt about it, but I agree with strandinthewind. If you like this guy, and think there could be something, then go for it.

I've never been in such a situation, but I would assume that no one would really be okay with one of their great loves becoming involved with their best friend. I see nothing wrong with it because she's the one that screwed up the relationship to begin with and she has no claim to him, but I would imagine that it would hurt quite a bit on some level to constantly be reminded of what you f*cked up and having to deal with the regret of your actions like that on an ongoing basis.

Potentially sticky situation, for sure. I would venture to say that your friendship would never be the same should you date him, even though her actions led to their broken engagement. From my own experiences, women get angry when you just so much as look at a guy they've been/are interested in. If you talked to her about it, I'd guess she'd say she's "fine with it," but it would probably bug her.

I think you should go out with him more, but don't tell her anything until you guys are serious. Yeah, you heard me, I said go out with him and don't tell her unless it gets serious! :woohoo:

I concur. :nod: Is your friend in love with her fiance? If so, this should be easier for her to take, should you need to tell her (if it gets serious). If she isn't, that's a whole 'nother ball of wax.

IMO, eventually you're going to have to choose between a 20 year friendship (is this your BEST friend?) and a relationship with this guy. If she is still hurting over the breakup, she will never forgive you. Even if it was her fault.
So, you will have to decide which will hurt you more: losing her friendship or losing this guy. I think it would be different if she were safely married (when is her wedding?) Also, what does HE have to say about what happened? Is he still hurting over her? A lot depends too, on how much of an attraction there is between you and this guy. If its undeniable, I say go for it! but then, Im the one that cant count how many people Ive kissed :eek:

My bit of advice would be to put yourself in her shoes. How would you feel about her if she dated one of your old flames? If you think you could manage, then go for it. But if you think you'd have a problem with the relationship, then I'd seriously have a heart to heart with yourself over this one. Without knowing you or knowing her, or the nature of your relationship, it's really hard for people who really don't know you to give you good advice.

Personally, I've always had a hands-off policy regarding a friend's old flame if that friend is someone whom I'm very close. But that's me. I don't think you'd be wrong to go for it, but be prepared to lose a longtime friend. And really, my own experience is that longtime friendships tend to end once one of the friends gets married. I've stopped being close to at least three of my close friends after they got married. They're in a different place than I, so it's just natural that we'd drift apart. So, if she gets married, there's no guarantee that you and she would be close in the future anyway.

You have a good point. See, I've never been in this situation. I can't even believe I'm in it now, even though it was only 1 night to the boat... 1 friendly night. Even though we hang out every great now and then, it felt like this was different. He and I have been good friends for about 12 years now. But, I know the tide could turn one way or another. I'm torn between- this is one of my best friends of 20 years, and/or, she did him wrong, it's been 4 years, and she has a fiance and a new baby. I just don't know. I feel like I'm damned if I do and damned if I don't.

Sorry but if I could add my 2cents?? If not just say so..but my take on your problem is....Your friend has moved on in life..she has a fiance and a baby? Sure she regrets the mistake she made..Who hasn;t made mistakes in life and not had regrets.?Butttttttttttttt.....if she is a good friend...wouldn;t she want her friend(you) to be happy? and also the man she was once engaged to ? also to be happy? and even if that means seeing the 2 of you together..if that happens..Or else she has not let go and I see big problems for her and her new life..Maybe you should have a heart to heart with her about her feelings about this guy..Is she still in love with him,? does she want him to be happy?etc...Just my take...Everyone deserves a little piece of happiness in life..For now go with the flow and see what happens..

I agree. It might not work out. But if it does, you have to take the chance of losing the friendship.
Life is short.:shrug:

Maybe I'm putting the cart before the horse. I just like to think about what might happen if.... And I have been up front previously with her about "hey I went to his house this weekend, so and so was there... blah, blah, blah" And she says she don't want to hear it. So, maybe I will shut up about it for now, and just see. I'm just afraid to get my toes wet.

Thanks for the responses. It's definately food for thought.