I spoke to a number of dating experts on the subject, and across the board they all echoed a similar sentiment: throwing a friend's ex into the dating mix can be a bloody disaster.“On paper, it sounds like an absolutely horrendous idea, and something most good friends would try to avoid like the plague,” notes Michael Valmont, a dating and social coach.When coming out of a relationship, a friend should be there as a strong supportive shoulder.“If they begin to date the woman you were seeing, it can feel like an extra knife in the back. My rule of thumb is that it's fine unless it is a very good friend.Particularly if you were in a long-term relationship with her,” he says. If it's just an acquaintance from work, and he dated a woman you like, they broke up, then there is no reason why you couldn't date her,” says Sebastian Callow, a London-based dating coach for men. Experts recommend considering how long your friend and his ex dated (anything over six months is tricky territory as the emotional ties tend to be stronger); how old you are (one expert suggested that in our twenties, perceived slights carry more weight than when we're older and “more realistic”); why you're interested (do you lack the self confidence to approach a stranger?But what if you really, really fancy Sally, to the point you're picturing sleepy Sundays and all sorts of lovely, luscious romance? ); how much stress you're willing to endure; and ultimately what the friendship is worth.
Nana points to the story of her friend Katie, a 27-year-old Londoner who lost a friendship when an ex got involved. Tell him what his friendship means to you,” suggests Irene La Cota, president of dating agency It's Just Lunch International.If you're swept up in love and you simply must date the ex of a close friend, experts recommend you sit your friend down. Even if it hurts your pride, check with him that it's OK. La Cota stresses the conversation is worth having if you really think the girl might be your 'special someone'.“And keep in mind that your friend is most likely going to say 'go ahead', even if he doesn't mean it,” she says.During the conversation, pay attention to your friend's non-verbal communication.“As guys, we often say we're OK with the situation to put on a brave face, when really we're anything but,” adds Callow.“Any hesitation or lack of certainty in your friend's tonality? Even if you really like the girl, “if your friend isn't cool with it, I'd still recommend holding back.” At the end of the day, dating a friend's ex is going to be tricky territory all around. If you can't, be prepared for potential complications and be realistic that you might lose a good buddy.“This is not an episode of Friends where everything seems to magically work out, despite love triangle after love triangle,” says Valmont. It's fun while it lasts, but the devastation it leaves after is not so pleasant.” So maybe step back from Sally, and go find a Jane, or Becky, or anyone else that isn't your friend's ex.“I hate the old cliché 'plenty more fish in the sea' but there really are more women out there,” says Callow. Does Gretchen Weiners have a point about the rules of feminism? So in your opinion, what are the rules about dating exes?I don't think those are the rules of feminism so much as the rules of human decency. That's some Dawson-Joey-Pacey kind of betrayal, and I can only imagine the level of hurt you've been feeling. We don't betray the ones we love the most, or at least we try not to!