I just broke up with my girlfriend a few months ago. Honestly, the relationship had been over for a while, so by the time the breakup actually went down, it was pretty friendly; we still talk all the time. She’s got a friend I’ve always found really attractive, and recently the friend mentioned to my ex-girlfriend that she’s interested in me too. My ex says she’s okay with it if we go out, but a couple of my girl friends tell me that I shouldn’t even consider asking her out, no matter what my ex-girlfriend says, so I’m not sure what to do. What do you guys think? —TM, Los Angeles, California
The straight man’s perspective: Chris Kennedy
I’m not a big believer in having a lot of dating rules, but I do hold true to the Golden Dating Rule—do unto significant others as you’d have done to you. Even if someone isn’t your significant other anymore.
I say don’t do this unto your ex. Put yourself in your ex’s shoes. Not literally—I’m not recommending fetishes—but see things from her perspective on this. I don’t care how over a girl I was, I’d have a pretty tough time if my ex started sleeping with my friend. Wouldn’t you? And wouldn’t it burn you that the only reason they know each other is because of you? That you were essentially a matchmaker? I don’t know how long your relationship was, but if it was of any significant time, this would be really awkward. Sure, you say you and your ex are friends now and talk all the time. But don’t fool yourself into thinking there isn’t more at stake here than just asking out the friend of a friend.
All you’ve said about your ex’s friend is that you find her attractive and you’re interested. “Interested” is not enough of a reason in my book to breach the Golden Dating Rule. If you said you thought she was “The One” and your “Soul Mate,” I might reconsider, but she would have to hold that sort of potential. Your ex may say she’s fine with it because otherwise she has to say no, look petty, and fight with both you and her friend. (What kind of friend says she’s interested in her friend’s ex, anyway?) Your ex knows that you guys could easily sneak off and have your little rendezvous anyway, so she’d probably just as well know about it. I want you to go after other attractive girls. You live in LA; there are a few around.
Take the high road here. Sometimes you have to walk it in someone else’s shoes.
The straight woman’s perspective: Rebecca Brown
For God’s sake, man, have you been awake, alive, or attentive on this planet—like EVER? NO, you cannot go out with one of your ex-girlfriend’s friends! Ever. No matter what she says or how little she promises it will bother her.
You get a few points for asking your ex if it’s okay. That was nice. But that doesn’t really help you. Because right now—whether she’s consciously aware that she’s doing it or not—she’s testing you and the definition of your newly defined friendship. From the way you describe it, you broke up with her. You know how it is after a breakup. She wants to look cool, like she doesn’t care. She does not want to look like she gives a rat’s ass about what you do now that you’ve dumped her. She’s being breezy—but without saying she’s breezy … that was the mistake Monica made on Friends, as I’m sure you recall. She’s so breezy, she doesn’t give a damn who you go out with. Of course you can go out with her friend! She’s breezy, damnit!
Do not be fooled, TM! She may seem breezy, but the second you go out with her friend, you are a marked man. Your friendship with your ex will never get off the ground—at least not until you stop dating her friends. And perhaps more importantly, you’ll be shunned and given skeezy asshole status by her protective posse of friends (as you should be), which means that minus her one rogue friend who’s actually dumb enough to go out with you, you’ll never date anyone else in her circle—or even six degrees of her circle. It might cause a little tension between her and her friend, but for the most part, we ladies stick together. Eventually, you’ll lose on both counts: your ex as a friend, and her friend as a potential girlfriend. Going out with this girl is insensitive and strategically stupid.
There are, of course, probably a few women in the world who really wouldn’t care, and maybe your ex is one of those women. Even so, I still say stay away from her friends. Swim in a different dating pool if you really value a genuine friendship with this woman.
The gay man’s perspective: Darren Maddox
First of all, if she’s interested in you, let her ask you out! She’s the one expressing an interest in you, after all. Or if you’re interested in her and you’re the one who always asks the girl out, then do it if you want to go out with her. You’re single and ready to mingle.
However, if you do go out with her be warned that it’s one thing for your ex to think she’s okay with you going out with her friend, but it may be quite another story when she sees you happily together. Emotions will likely come up that she never knew she harbored. Just be aware of that.
As far as your friends go, unless they know her friend better than you do, I would ignore their advice. Who knows? This holiday season could turn into Miracle on 34th Street or The Nightmare Before Christmas. Either way, if you want to take a chance, and you’ve discussed it at length with your ex girlfriend, then go for it.
The gay woman’s perspective: Jody Fischer
It’s funny, lesbians are notorious for dating friends of their exes and exes of their exes. It never quite sits right with me. Let me ask you to answer the following question to see if you’re really ready for this:
What are you most concerned about here?
A) Protecting yourself
B) Ruining the friendship between the two girls
C) Having them compare notes on you and how you kiss
D) All of the above
If you selected D, congratulations—that’s the correct answer! Let’s review all the answers in reverse order.
C) If you think that they won’t talk about you, you’re wrong. It will come up, I promise. They may discuss your assets, but I’m guessing they will spend more time talking about your ass and other intimate info.
B) You ended it with your ex. I don’t care how buddy-buddy you are with her now, unless she’s super evolved, she’ll feel badly that she couldn’t make it work with you and that her friend may be able to. It’s very likely that you dating this other girl will affect the quality of their friendship.
A) She may say she’s okay with it—and I do like to take people at their word—but I find myself siding with your other girl friends here. You may lose your friendship with your ex over this, which could upset her friend … which may lead to the friend breaking things off with you.
Your decision may come back to bite you in the ass. If you value her friendship, which it seems like you do, look elsewhere for some lovin’.