Can You Date Your Friend's Ex?

Yes. Yes, of course you can date the ex-partners of your friends. Of course you can. The question should really be, is it possible to keep your friend in the process.

We've all been there. We've all had friends with failed relationships. And as good as the friendship is, sometimes that ex is just too tasty to resist. We all know there is no cut and dry answer to this dilemma. Sometimes this is do-able. And sometimes it isn't. Some people are highly possessive regarding their ex's. Many years ago I dated the ex of a friend's cousin. It wasn't even my friend's ex. It was her cousin's ex. And the fall out was unbelievable. But in happier news, I had another friend who actually hooked me up with an ex of hers. That worked out fine and fun for all.

I could start with all that sappy obvious stuff, like saying: The first thing you really need to ask yourself is, how important is this friendship? Is this someone you've known through the gym for a year, or is this a long term 3:00 in the morning phone call - knows your favorite vodka as well as your favorite former teen idol - kind of friend? If this is a friendship worth fighting for, than fight for it. Fight the urge, and get over it.

Let's assume you've got 2 brain cells to rub together, and you've already assessed the situation. This is a good friend, a 3 AM friend, and still you find yourself texting The Ex, or casually trying to crash his weekly happy hour at a local bar.

One of the reasons you have a friend who's heard you admit you still kinda dig Matt Dillon over 3 Grey Goose Dirty Martini's, is honesty. You can let your hair down and be frank with her. You can tell her she has broccoli in her teeth. You can tell her you spent the rent money on a massage. Now is not the time to stop.

Remember how it felt to be in her shoes. One of the worst things about being dumped is that stupid feeling. Even if you saw it coming, you didn't really see it coming. Not really. So when he told you he wanted out, you were blindsided. You felt dumb for not having known he was unhappy.

Assume that's how your friend feels. And try to imagine how much more magnified that feeling would be if you make her feel stupid too.

I suggest a pre-emptive strike. Let her know. Immediately. Yeah, it's gonna hurt her, and she will feel open and raw. But when day is done she will still have her dignity, and that goes a long way. Be truthful with yourself: you wouldn't want your so-called friend sneaking around behind your back. The odds are, neither would she. You know how she feels about the ex, you know how she feels about you. Much of the sink-or-swim of this, will rely on how she feels about herself. And that is the hard part of the break-up. If you make her feel bad about herself, she will excommunicate you.

Making her feel good about herself is NOT about idiotic flattery and fake empathy. All you need to do, is keep three goals in mind, for every sentence you speak:

1. Do not get dragged into a tit for tat about her failed relationship.
2. Do not compare.
3. And do not ever imply that you can succeed where she failed.

Do not get dragged into a tit for tat, this for that, he said she said - kind of conversation. If she wants to point out how he never called when he would be late, do not defend him and point out that her version of late is 25 seconds. If she tells you he didn't want to meet her parents, don't remind her about 10 years ago when she faked an appendicitis to get out of having Easter dinner with her then boyfriend's father. You can't make the light bulb over her head suddenly illuminate where she says, "Oh you're right. What was I thinking? I was wrong, and you deserve him."That's not going to happen. So don't argue. Don't combat every point she makes with correction or an attempt at balance.

When she says he was always late, be her friend. Not the potential new girlfriend. Not her teacher. Not the judge. Just be her friend. Just nod. If you feel you have to say something, then sympathize. "That must have been frustrating." If she says he wouldn't meet her family, just nod. "I know how close you are to your family." If you don't give her a reason to fight harder, she won't. She wants to be heard. That's what that whole Venus woman thing is about, right? She wants you to hear her. So, hear her. She wants to feel better. Just let her. And be the friend you have been, not the girlfriend to the ex that you want to be. You don't have to take sides. If she really pushes for you to admit a more sided response, bow out. Shrug. "I wasn't there. I don't know. But I can see how bothered you were by it."

Do not compare. Ever. Do not compare how much better you would handle something with this guy than she did. Do not compare your past relationships to hers. Do not compare her past relationships with this one. Do not compare anything. And don't let her. Dismantle any comparison she attempts. If she starts comparing: "You are such a stickler for punctuality! You'll be even more upset than I was!" Just nod. Shrug. If you point out all the reasons why you won't get upset like she did, you're comparing, and you're making her fight back. Don't do that. Don't make her fight.

If anything, justify her. Justify her feelings, her intentions, even her initial attraction. If she says, straight out: "If you know all the bad things he did to me, then why in the world do you still want to go out with him!?" You have one response only.

"Because I see what you saw in him. I'm where you were when you met him." You understand why she got involved with this guy in the first place. She was attracted, like you are now. Just point that out if you're pushed. And don't go any farther. You aren't better than she is. You aren't going to learn from her mistakes and succeed where she didn't. You're just like her. At least, let her have that much.

And that brings me to my last point. Do not imply that you think you and the ex can have success. If she asks you if you really think you can make this work, don't say yes. Do not say yes! It's practically throwing down a gauntlet. The very best you can do, is put yourself on her level. Put yourself where she is, just in a different spot on the time line. You can say, "Maybe a month from now you'll be the one buying me martini's."

Let her see you as her friend, not as his girlfriend. At least, not yet. When she complains about him, leave it at that I hear ya, sister! feeling.

And the truth is in the beginning stages, you really don't know. She may be 100% right, and you may be exactly where she is in a few months. I do think it's possible to maintain your friendship while you go out with the ex. As long as you do it with care.

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All text is original content by Veronica.

All photos are used with permission.

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