Un-Sloppy Seconds: A Case For Dating Your Friend’s Ex

Posted by By Tracy at 15 June, at 11 : 19 AM Print

Un-Sloppy Seconds: A Case For Dating Your Friend’s Ex

Let me preface this blog with a quick, but tricky request: muzzle up your pretty little ego.

Please and thank you.

And, you’re welcome.

Okay, hi. Six months ago, this random dating query bounced down my Twitter timeline—Is a friend’s ex completely off limits? As expected a parade followed the first pied piper who RT’d with “ALWAYS!!”

Just in case you missed it, that response was donned in all caps, two exclamation points and I’m pretty sure if Twitter offered italics, those sloping b-tches would’ve had their shine too.


Actually, I understand. It’s suspect to say otherwise, but the truth is there are exceptions to the damn rule. And if you don’t consider that a fact, it’s time to exercise some damn utilitarianism and be empathetic to the fact that sh-t happens.

(Your asses better not think I’m out here tossing every last piece of penis from Cece and Guerd’s past into my shopping cart. Hell no!)

I think we can all assume that falling for a pal’s former flame wouldn’t be an ideal matchmaker setup for anyone. Really, who wants to go out of their way to be tagged the bad guy? Sure you may actually have a sleezy ex and a sleezy buddy who secretly smashed to the point of convenient memory loss. That happens as well, but I’m not defending those two, and I’m pretty sure they wouldn’t defend themselves either, because well, actions in the name of barbaric lust are difficult to rationalize.

But when it comes to dating, aka publicly demonstrating a romantic interest in someone, and wanting to hold someone’s hand that once touched you know who in you know where, takes a chunk of courage. And beyond that it takes a genuine connection… some shared flame the bad guys are willing to bet won’t be easy to extinguish. So why be territorial about expired property?

Damn this is a touchy topic…

Please note: I am not advising anyone to plot in advance how they’re going to pounce on a friend’s ex (especially if they’re still in a relationship!). I am not advising anyone to look at all their friends’ exes as equals to the anonymous suitors out and about in these streets. I am not advising anyone to date a friend’s ex knowing there’s a fresh wound still bleeding on the table.

What I am advising is this: Evaluate, then reevaluate, then re-re-evaluate before taking a leap of faith and stepping out into a downpour of awkward moments. And if you don’t consider dating him or her a leap of faith, then why even do this sh-t?

But if you are in fact leaping, here are two bullet points to consider for semi-smooth sailing:


Well it’s partly breaking news, but then sorta asking for your friend’s blessing, but still, make it more about you breaking news. Remind yourself that it’s not like they gave birth to this person. And of course the longer the relationship has been defunct, the easier this conversation will be. Just be honest and tactful, and most importantly don’t procrastinate. The moment you wouldn’t mind kissing this person while waiting for the train to arrive or perhaps after you’ve just kissed this person while waiting for the train to arrive, is when that talk needs to happen. Our personal six degrees of separation are forever alive and well, so don’t let a brow-raised bystander tip off your pal before you do.


When at a get-together, be natural, but classy. Even if your buddy flashes you two thumbs up, it doesn’t hurt to act like their ego hasn’t completely thawed out. This is the only time, I’ll support pandering by the way, only because what’s an hour or two of restraining from PDA when you’ll be spooning till Sunday afternoon with the person you arrived with? Remember that this is an adjustment period for not only that one friend, but your curious mutual friends as well. Consider it the fine print you signed up for and ease up on the cyber displays of affection as well. You can do it.

Fun fact: In April I went to a wedding where the bride’s ex-boyfriend was one of the groomsmen… and said ex-boyfriend is also an ex-boyfriend of mine hahaha. One big happy family.

I really could go on and on about this talking point, because it’s so particular to the three people involved. Even if you’re more on the unconventional, free-spirited tip like me, there’s probably at least one beau from the past that’s been branded as “untouchable.” And you know what? Have that. Just so long as you let them other exes roam free—after all, you can’t own em all.

Don’t side-eye the messenger!

Tracy (@trayhova)


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  1. I would personally never break this rule. However if one of my friends dated one of my exes, I can respect it if a she would come to me first before I hear it from someone else but I just feel like there are so many guys in this world, you honestly do not need to go after my ex but I understand shit happens so I would be willing to forgive my friend depending on the situation.

    Kelli, 2 years ago Reply

  2. I just can't agree with everyone on this topic. I am not a girl with a lot of exes so if you are really my friend you would never cross that line with my ex. I just don't think that is okay but I respect everyone's opinion!

    Diane, 2 years ago Reply

  3. thank you for talking about this topic! I honestly think it is okay to go after a friend's ex if you really have true feelings for him and you strongly believe it could develop into a long term relationship. I would just say be honest to your friend and please never take it to the next level until you have spoke to your friend. You do not necessarily need to ask for permission [I always do] but you don't have to, you just seriously need to give them the heads up.

    Mia, 2 years ago Reply

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