Deep Dive: Is It Bad to Sleep With My Friend’s Ex?
If you’re lucky enough to have a friend, at some point you likely met one of his girlfriends. The best-case scenario is that you get along with your pal’s new partner and enjoy her company just as much as you do your buddy’s. You may even find yourself attracted to her. But like a good friend, you squash your sexual impulses because you’re not a bird dog. Then their relationship implodes, and in the wake of their breakup, you may find yourself wondering about your friend’s ex — and whether or not she’d be interested in spending some one-on-one time (preferably naked, in bed) with you. Is it totally skeevy to pursue her? Or is all fair in love and war (and sex and friendship)? In today’s deep dive, we’re asking: Is it bad to sleep with my friend’s ex?
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How long were they together?
The length of your friend's relationship with his ex is key in determining if you can make a move or not. If they were ever engaged or married, that's a hard stop. If they were in a long-term relationship, it may be possible to proceed with caution. If they only dated a few weeks or even months, plow right on ahead.
How long have they been apart?
The longer your friend and his ex have been broken up, the better. Heartbreak heals with time. If it's been a year or more, you're probably in the clear. A few months? OK, give it a shot. If the breakup is still so fresh that you're among the select few who know about it, it's way too soon. Give it a minute, man. Let the loins, tempers, and emotions of both parties cool.
What is your friend's relationship status now?
People take breakups differently. Some can move on in a millisecond while others need to grieve for years. It'll help your case tremendously if your buddy is already ensconced in a new affair. If he's in a relationship or seriously dating someone new, he's less likely to have objections about you infringing on his former turf. If he still suffers from "mentionitis," stalks his ex's social media, or reminisces incessantly about her, he is in no way ready to hear that you want to bone her. Be a good friend and turn your attention instead to helping him get laid. After all, they say the best way to get over someone is to get under someone else, right?
How close are you and your friend?
The more buddy-buddy you are, the tougher it's going to be to rationalize bumping uglies with your friend's ex. If you two are seriously bromancing, it's going to feel like a betrayal. But if you're friends from, say, elementary school who have grown apart or just recently met and only see each other at the occasional group function, your friend is less likely to feel wounded by you lighting a fire with his former flame.
Have you talked to your friend about it?
They say that you can ask for permission or you can ask for forgiveness. Either way, you're going to have to talk to your friend about this (or feel really shitty, in secret, forever). Telling him you'd like to see where things lead with his ex is definitely classier than dropping a truth bomb later that you banged the only woman he's ever loved. In a perfect world, you'd be completely honest about your attraction to his ex and give him a chance to veto your seduction plans -- but you'd also have to have enough self-restraint to actually respect his wishes, no matter what they are.
Are you prepared for scandal?
No matter how this pans out, people are going to talk. If you sleep with your friend's ex and things end horribly, she'll blab. If things go well and she ends up as more than your fuck buddy, you're going to get the side-eye from everyone who discovers you're a couple. A guarantee: no one is going to be slapping you on the back. Can you handle being the bad guy?
What are your alternatives?
Have you truly given the search for a fling the old college try? Have you swiped right on every possible match on Tinder? Do you have your own ex you could hit up for some no-strings-attached action? Before going straight for your friend's ex, make sure you've exhausted all other casual sex options. If the ex were that special, wouldn't you be interested in more than sex anyway?
Sleeping with a friend's ex is risky business. You're potentially putting your friendship on the line, not to mention your reputation and the ex's feelings. It's a loaded situation, and one that might not be worth the drama. Sex is fleeting, after all; shame lasts forever.
That said, if you feel compelled to bed your friend's ex, at least do so in as classy a way as possible. Be upfront with your friend, respect his boundaries (i.e. he probably doesn't want the morning-after play-by-play), and don't be a dick to the ex. Basically, be on your best behavior (which doesn't sound that sexy, does it?). If you really want to behave badly, but save yourself the headache, go find some stranger who's ready, willing, and easy to leave behind.