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.
