“You can try to handle it like an adult, being open and honest – but you will go down a notch on the friendship ladder,” agrees Nana Wereko-Brobby, director of Social Concierge, a London dating service.
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.
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.
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.