The Reckoner!

Help Reckonauts! I broke up with him, I'm not over him, and he asked my best friend out! What should I do?

I really need your help to deal with this relationship situation because it is tearing me apart.

Recently, I broke up with my boyfriend of five years. It's been almost a year since the break up, and I'm still not over him or us for that matter. I am embarrassed to say that he has moved on, but I have not!

The problem is that he has asked out my best friend, who informed me that she will not consider going out with him unless she has my blessing. She has been my best friend since elementary school and we even went through college together. My boyfriend and I double-dated a lot with her then boyfriend and her, and I always knew that they really liked each other. Personally, I feel that she was more his cup of tea than I was. She has been alone for quite awhile now, and I realize that I need to get going again with my life. It just hurts so much to think of the two of them together.

What should I do? Please help me make this decision!

Reckoning Results!
Give Her the Go
Tell Her No
Move on!
Too awkward!
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Soda or Pop?

Reckoning Comments!

What makes this especially tough is that you dated for five years, which is an extended relationship.  You don't mention why you dumped him -- I'm guessing there was some fundamental incompatibility, or perhaps an unequal investment in the relationship given that you're still pining for him -- but I can definitely understand why it's tough.

I'd give her the 'Go'. And that's from a purely pragmatic standpoint, which is that the heart wants what it wants.  Your friend has been kind enough to ask you for 'permission', but this isn't a blood pact -- you're putting your friendship in an even more awkward position if you say 'no' than if you say 'yes'.  It has been a year, and as counterintuitive as it seems, seeing them happy together may actually help you bring closure to that part of your own life.

I'm with Mr. Koch on this - it's awkward but I'd consider your friend's request to be more "please tell me if this will KILL YOU; otherwise I want to date him" rather than "Either way is fine by me." In the end, this is a classic case of "Kinda sucks either way, but here's the way that'll probably suck less."

Diclaimer: I once dated a girl; we got about as serious as you can get in a year, but it became clear that we had major incompatibilities that would only get worse over time, so I broke up with her. A few months later, she alerted me that she was starting to go out with a good friend of mine. I don't think she was asking for permission per se, just giving me a heads-up, but I didn't see myself as having a right to intervene even if I'd wanted to - besides, I'd moved away, and they're still together 5+ years later, so it looks like things have pretty much worked out for the best.

If she is your best friend then I'm with Dan and Ben on this. Best friends want each other to be happy and if he would make her happy, I think you should try to be supportive of that.

I don't know. If I were the best friend and it really was hurting my friend to have this guy she used to go out with hanging around, I would be honest with her--that'll it be hard for you, but if she really really likes him, it's ok with you and you'll try to deal with your feelings. I agree with Catherine that best friends want each other to be happy, so, presumably, she also will want you to be happy--and that might mean passing on this guy.

Honestly, the person I am questioning here is the "best friend". Cant see myself even considering to date a friends ex...especially if they were serious. But if you guys really are best friends and I am missing something here, each other's happiness should be priority.  I say give her the "go ahead" but consider moving on from both of them.

If this "best friend" is truely a best friend she would know- best friends confide in each other about everything- that this person still has strong feelings for her ex; therefore, she would not even present her with this problem and cause her to have all this angst. It seems to me that the best friend is putting her feelings before her friend. She shouldn't have even asked her friend's permission to date this guy....better she should have informed the ex that this could cause an awkward situation and bad feelings between her and her best friend....I agree with what Patti said.....

The Reckoner!