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I really like my friend’s recent ex-boyfriend. To be honest, I liked him all through their relationship. Is it OK for me to date him now? I haven’t asked her yet, but even if she says she’s down with it, can I believe her? And, if I decide to go for it, how long should I wait?
—Crushing in Boston, MA
First, let me congratulate you on winning this week’s award for Cool Chick. Why? You didn’t try to sabotage your friend’s relationship or hook up with her boyfriend while they were together and you already know that you are going to have to put on your big girl pants and have that supremely awkward conversation about pursuing the ex.
People often place so much more value on their romances than they do their friendships. As soon as a hot guy or girl shows up, friends fade into the background only to be recalled with great need and urgency on the occasion of a breakup. As much as we would like to believe that true love never dies, the reality is that platonic bonds are often more durable and nourishing over the long haul than romantic relationships—but such deep friendships take prioritizing. Part of honoring your friend is asking her permission to go out with her former boyfriend.
If she’s still actively grieving, the right thing to do is wait. You waited out their whole relationship, what are a couple more weeks (or even months)? Take her out for a latte, and be honest about your feelings. Acknowledge that you have something potentially uncomfortable to discuss and emphasize that your friendship is extremely important to you. Odds are, she isn’t going to give you a big hug and tell you to “go for it!” but hopefully she’ll understand and appreciate that you were up front with her. If she flat out says, “no,” give her a few days to reboot and then have another girl-to-girl chat.
If you do end up dating the ex, expect some tension. It will ease over time. If she’s as good a friend to you as you have been to her, she’ll do her best to chill. Outings without the ex are crucial, and the occasional, “So, this is sort of weird, huh?” will afford her the chance to vent and clear the air.