It doesn’t have to be an “ask” so much as a heads up to let them know your intentions.If the friend does have a problem with this, the choice to mess up the squad is completely up to you.Dear 4-Way, I just broke up with my girlfriend a few months ago.
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 strategically stupid.
) 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. NO, you cannot go out with one of your ex-girlfriend’s friends! No matter what she says or how little she promises it will bother her. 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. She may seem breezy, but the second you go out with her friend, you are a marked man.
You get a few points for asking your ex if it’s okay. From the way you describe it, you can go out with her friend! Your friendship with your ex will never get off the ground—at least not until you stop dating her friends.
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.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.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. —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. Not literally—I’m not recommending fetishes—but see things from her perspective on this.But don’t fool yourself into thinking there isn’t more at stake here than just asking out the friend of a friend.