Is it ever OK to date your friend’s ex?

When it comes to dating your friend's ex, timing could be everything. JGI/Jamie Grill

If you’ve ever found yourself yearning for a friend’s ex, you know that it’s a precarious situation to navigate. All good friends like to believe in the mantras of “mates before dates,” and “sisters before misters,” but sometimes, the possibility for a true love connection is hard to ignore.

While it’s true that it’s not an ideal scenario, it’s also not an impossible one, experts say.

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“There are no actual rules when it comes to dating a friend’s ex, but it does require exercising some common sense,” says Natasha Sharma, psychotherapist and author of The Kindness Journal.

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Communication is vital if maintaining the friendship is important to you. Relationship expert Chantal Heide says it’s as much about hearing your friend’s words as it is about looking behind them for emotion.

“A lot of people can fake strength,” she says. “Don’t just listen to what they’re saying, read the emotion. Anyone can say, ‘I don’t care if you date my ex,’ but you need to listen for sincerity. Indifference is the opposite of love.”

A good way to gauge this is by suggesting an outing where your friend and their ex will both be present. If your friend has just said they “don’t care” if you date this person but then puts up a fuss about being in their presence with you, that’s a red flag.

“If you were dating a complete stranger, would your friend react this way?” Heide asks.

If you’re sensing some reticence from your friend but still decide to go ahead with pursuing the relationship, you need to ask yourself some crucial questions.

“You should first determine if your friend and their ex have broken up or if they’re on a break. Because if they have a history of breaking up and getting back together, you could be ruining a future for them,” says Richard Tatomir, certified counsellor and founder of Relationship Experts Vancouver.

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You also need to ask yourself if the ex has had enough time to heal from the breakup or you could risk being the rebound.

“Do some serious introspection,” Tatomir says. “How well do you know this person? Do they check off most of your boxes? Do you have strong indication that they reciprocate your feelings?”

It can come down to timing

A lot depends on the length of time your friend was with this person. A couple of years and a couple of months are two very different time frames and carry different sensitivities.

“A couple of months is a trial period, not a relationship. You should be able to say to your friend, ‘I ran into him [or her] and we’re going to go out for drinks.’ No one should be falling in love in a couple of months,” Heide says.

“But if they were together for more than a year, that means there were real emotions involved and dreams for the future.”

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Sharma frames this in the context of grieving.

“There is scientific research about how long it takes to grieve the loss of someone. In the case of a marriage that was valued and ended, it can take up to two years to grieve that loss,” she says. “That can be helpful in understanding your friend.”

You may have to choose between your friendship and your possible romance

Sharma says there’s an implied social contract between you and your friends that involves being open and honest.

“If you happen to be attracted to a friend’s ex, it warrants common sense and social sensitivity. Have a conversation with your friend first, so they’re not taken by surprise.”

But the reality is, your friend may strongly oppose the possible union and you’ll have to choose between them.

“If your friend isn’t OK with it, they’ll cycle through feelings of yearning, resentment toward you and their ex, and jealousy,” Heide says. “It will erode your friendship and affect your relationship with your love interest.”

It comes down to how you view your friendship — only you can answer which is more important. But Sharma also warns against being guilt-tripped into following the “girl code” or “bro code.”

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“That’s silly because it implies that you own someone. It’s irrational and territorial,” she says. “Any person who subscribes to a ‘code’ that says an ex is off-limits has control issues.”

Whatever you do, don’t ask for permission

You may feel tempted to talk to your friend about potentially dating their ex and phrasing it in a way that implies you’re asking for their permission, but that’s not the right tactic, Sharma says.

“Once you ask for permission, you’re giving up control and buying into the whole ‘code’ idea,” she says. “Everyone is free to date whomever they want and under any circumstance. There may be consequences to your actions, but no one can tell you straight up, ‘No.'”

She suggests discussing it with your friend and framing it in the context of consideration.

“Say to them, ‘I have something I want to share with you and I’m very interested in how you feel about it because your feelings are important to me,'” she says. “That’s being considerate without having to ask someone if you’re ‘allowed’ to date this person.”

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