A
male
age
30-35,
*urch
writes: So, almost a year ago I dated my now ex for about two months. It doesn't sound like very long, but we were friends for a very long time before we started dating and I guess that's why the break up had more of an impact than most two month break ups. Anyways, in that dating period I introduced my girlfriend to my good friend, we'll call him Jesse. After the break up things got awkward between me and the girl and we're no longer really friends. Jesse kind of helped me through the break up when none of my other friends really did, and so now I call him my best friend. So Jesse and my ex still remained friends and recently they've become pretty good friends. On more than a few occasions I've had to hang out with both of them at the same time and its been very awkward for me and her. I don't think Jesse really notices. Anyways, about a week ago Jesse told me he had a crush on my ex. He is a really good guy and he asked me if I was ok with it and I said yes. I'm not sure If I'm 100% ok with it, but I didn't want to be "That guy". Don't get me wrong, I don't think I want to date her. I just feel weird about it. So, now he's been "going after her" for about a week and today was just kind of worse than usual. We all hung out, he was flirting with her, and I just didn't feel well. Jesse asked one of my ex's close friends if my ex would go out with him if he asked her. My ex's friend said that my ex "isn't ready to answer". Here's the thing, I don't think my ex actually likes Jesse. I think shes stringing him along. She has already been stringing one of my friends along for several years. I got to know her very well in the past and I know the signs that she shows when she likes someone. She isn't showing any of them. The main reason is: She's very superficial, and Jesse isn't the best looking kid. So overall, I'm worried that they might date and I'm worried that she might hurt my best friend. I don't see any outcome that ends well
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best friend, crush, flirt, my ex, period Reply to this Question
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male
reader, Murch +, writes (19 March 2010):
Murch is verified as being by the original poster of the questionHe hasn't actually asked her yet. He told me he was going to several times before, but that time it seemed more serious and more probable then any of the others.
I definitely agree with you Tisha. I just need to ignore it and take myself out of that position. Which might be hard to do if I still want to be friends with Jesse. I'm not sure what you mean by "managing his reactions to her". I guess I was acting like a mediator in a lot of ways. Trust me, that has stopped.
I think hanging around more with other friends is probably the best thing to do. It doesn't exactly make me happy, but neither does my best-friend dating my ex.
I don't really want to accept that he's picking her over me but I guess that's just how it is. I do know what "laissez faire" means , and you might not believe it based on all my gripes on this site but that's pretty much how I live my life. This girl just has a really negative affect on me.
Thanks again Tisha
A
female
reader, Tisha-1  +, writes (16 March 2010):
 Sorry to hear that. The problem is that you're too into the situation and need to step back and do your best to stop watching it. You also have to try to stop managing his reactions to her. You can't win here. I guess what I'm struck by is your feeling that you somehow are a mediator between her and him. You have to step out of that self-imposed role here.
She is who she is and he is who he is. They will either work out or they won't. He has to do his own learning and his own explorations, even though you have prior knowledge and firsthand experience with her, this doesn't mean that it will be a replay of your relationship with her.
In a sense, he's chosen her over you, and I think it would be a good idea for you to hang around with other friends for a little while, until things shake themselves out.
Chances are, their relationship will end with drama as well and it would be better all around if you had no role to play in that drama, even as a bit player. Just leave them to figure it out for themselves.
I am sorry he's picking her, but these things happen and in the fullness of time, you will know who will be a lasting friend. Try to remove that knot of anxiety about it from your belly and replace it with a 'laissez faire' attitude. If you don't know what that means, well, that will give you something else to focus on for a while.
Hope things go well for you.
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A
male
reader, Murch +, writes (16 March 2010):
Murch is verified as being by the original poster of the questionHe's going to ask her out tomorrow
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A
male
reader, Murch +, writes (15 March 2010):
Murch is verified as being by the original poster of the questionThanks Kenj,
I guess I should just see it through, and be there for him.
Thanks a lot for writing Tisha,
I've taken your advice, and I told him that me and my ex aren't friends and that its very awkward every time we hang out. He was pretty understanding.
He still likes her. I wasn't going to change that. He still wants to ask her out which I'm not completely heart broken about. She has shown a little more interest in him lately and I think she likes him.
I didn't think I described her a lot or very well, but you somehow have a very good grasp on who she is. I just wish there was a way to separate her from my life completely or at least tell Jesse who she really is without sounding jealous.
This whole thing is really stressing me out.
Anyways, thanks again Tisha
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A
female
reader, Tisha-1 +, writes (12 March 2010):
The truth of the matter is that you ARE "that guy." You lied to Jesse about it not bothering you. It does, or you wouldn't be here. Jesse can look after his own heart, and he does know about her history with you, he's a big boy now. Let him make his own mistakes. If he has to experience the bitterness of having her break his heart directly, and not just vicariously through you, well, that's actually HIS problem.
I think the mistake you made is not coming clean with him about it. You could go back to him and just tell him that this thing between him and your ex makes you feel awkward and uncomfortable. Tell him since you and she aren't really friends, this will distance you from Jesse if things would work out between them. It's okay to be honest in that way.
Right now, Jesse is thinking you're cool with everything and that simply isn't the case. Eventually, you and he are going to have this out because the pressure of the situation is going to make you miserable and you will act out, one way or another. You could point out all her flaws and the fundamental problem with her, which is her lack of integrity and honesty. Wouldn't it just be simpler and more honest all around to tell him the truth?
Don't worry about Jesse's feelings, they are HIS problem. Be honest about yours, or you and Jesse won't manage to be friends for much longer if this thing with your ex actually results in them having a romantic relationship.
She sounds like an energy vampire to me. I'd distance myself from her as much as possible just to preserve my own sanity.
Good luck.
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A
male
reader, Kenj  +, writes (12 March 2010):
 You cant really fix this, if you tell Jesse this he will think your just trying to split them up. The best thing you can do (and I know its hard) is let things take their course.
If and when Jesse gets hurt, be there for him as he was for you. It may work out different between him and her than it was for you and her, everyone is different.
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