7 Tips for Dating Your Friend’s Ex

Is Your Friend’s Ex Off Limits?

If you’re thinking of treading on the thin line between your friend and their ex, she or he must be an awfully special catch. At least you’d better hope so, considering these seven layers of yellow tape that could be blocking your entrance to a happily-ever-after:

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Clouded Judgment

Just as the 80s song by Rick Springfield suggests, you may wish you had “Jessie’s Girl,” but there are likely some psychological mechanics at play. She/He has basically already been approved by your friend, so you’ve likely heard all the great stuff about them, which is going to make you swoon a bit more. They were also formally located in forbidden territory, but now that they have relocated into that gray area, you may be drawn a little more to that apple tree. Just keep in mind that these decisions tend to squeeze the goodwill out of a friendship, so understand that your friendship may never again be as close as it is now. If you’re okay with that possibility… then read on.

What’s Really at Stake?

There may be a lot of unspoken rules to dating a friend’s ex, especially when you are a loyal person, but nothing makes the gray area more oblique than a friend who really isn’t all that close anyway. No offense to the friends hanging out on the second rung of the ladder, but sometimes love calls and you’re just better off answering back.

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The Waiting Period

Rejections and breakups can be painful no matter how long the relationship lasted, but they can be particularly heartbreaking when the relationship was halfway towards the one year mark. In the case of a more long-term relationship, it is always a good idea to put a comparable amount of time and space between any moves you’re considering.

Is the Breakup Permanent?

There are a fairly high percentage of couples who break up only to end up back together again. Do you really want to find yourself in the middle of an on-again, off-again romance? This is why it is always best to give any breakup a cooldown to see where things are headed before making alternate plans.

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Risk Assessment

If your friend made the decision to break up with their ex, their emotional state might be slightly less charged and they may not mind you dating their ex after a couple weeks. If your friend was hurt by the breakup (perhaps their ex cheated on them), then taking sides with the enemy at any point might be seen as a strike against friendship loyalty. How can your friend ever root for your happiness, when they are scouring their ex’s Facebook page hoping for signs of distress. Which brings up an important point: If they did break it off because of something bad their ex did, what makes you think the same won’t happen to you? Are you really sure the good sex you’ve heard about will justify the risks you’re taking?

The Talk

Before you put any effort into getting to know a friend’s ex, you need to have “the talk,” especially if you have any hopes of keeping your friend over the long haul. The best way to kick this off is to be honest with them about your feelings. Explain why you would like to date their ex, and this is also the point where you should really look for signs of distress, annoyance, irritation and possibly a little anger. It is important that you know their true feelings before making any rash decisions.

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New Love

It takes time to get over an ex, and everyone recovers at their own speed. However, research suggests that when somebody finds a new love interest, those previous emotional ties can be quickly severed with the excitement of new opportunity. Dating your friend’s ex after your friend has already found a new relationship won’t be nearly as emotionally traumatizing for your friend. In fact, they could be so happy with their new relationship, they would be able to wish you well and actually mean it.