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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.During their relationship you found yourself developing feelings that went far beyond a physical attraction.You two just “clicked.” Fast-forward: Their relationship ended, she’s single, now what?Jennifer Aniston and bestie Courtney Cox were both romantically linked with Counting Crows frontman Adam Duritz - and Katy Perry and Taylor Swift both had relationships with John Meyer (though that one did cause Bad Blood).Simply say, “Look, I just thought you should know that (their exes name) and I have gone on a few dates.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.
Let me say once more, it’s never going to be the best idea you had, but if you honestly do believe their ex is your future love of your life, here’s how to have the best shot at keeping the friendship You’ll probably get one of three reactions: they’ll be genuinely happy you’ve met someone you really like and won’t care; they’ll be upset and may well walk out; or pride will make them say, “Sure, go ahead! You’ll be strongly tempted to gossip about the person you both know, each repeating what they said about you (never dreaming you’d end up going out) and be massively curious about how their relationship was and how you compare.Post-college dating, especially in a city like New York, is challenging and frequently ego-depleting.Thanks to online dating websites and applications like Tinder and Hinge, it’s feasible to have seven (or more) dates per week.I have done it before and always, the brother gets involved and I can't be bothered with it.It can lead to complications in friendship if things don't go to well.
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?