A Choose-Your-Own-Adventure Guide To Sex With Exes

Relationships end for a reason. Severing is painful, though, and the loneliness that accompanies the end of a relationship can make you doubt your decision, and sometimes even flip-flop and end up back together.
Publish date:
June 28, 2012
breakups, Dating, exes, double-dip

Relationships end for a reason. Severing is painful, though, and the loneliness that accompanies the end of a relationship can make you doubt your decision, and sometimes even flip-flop and end up back together. It's not often that those reconciliations last very long, but it does happen.

For me, during the period directly after ending something substantial, the idea of starting from scratch sounds like cruel torture. Going out on first dates seems absurd and exhausting. I just spent a year letting someone get to know me and my neurosis, and now I have to stuff it all away again and be charming AND somewhat normal? Think I'll wait on that for a bit.

The time after a breakup is a great time for the following: stress-enduced-and-confidence-boosting weight loss, irrational spending, reconnecting with and making new friends, and sex with people you don't want to date. These people can be one-night stands, NSA sex buddies, or my personal favorite: the Double-Dip.

The Double Dip Golden Rule: If they’re saved in your phone under something similar "NEVER AGAIN", it’s probably not a good idea.

verb [ no obj. ] informal

1.obtain an income from two different sources, typically in an illicit way.

2.The act of dipping a chip, taking a bite, and then dipping a second time, into the same dip

3.Casual sex with someone you used to date.

Double dipping can be very successful and very, very fun, but it can also be a nightmare if you don't follow the rules.

When you DD, there's no getting to know you phase, and no awkward first-time sex. You know each other’s likes, dislikes, kinks and post-sex behavior. There's also nothing at stake, and so your relationship is more likely to be honest, and honesty + communication = best sex ever. (Believe it folks, it’s MATHEMATICAL SCIENCE!)

Most importantly, unlike the one-night stand, presumably you both care about each other. Meaningless sex is fun, sure, but in my opinion it is not as fun as NSA sex with someone you know values you a person, and respects you. This also makes the sex a lot safer, in general. That being said, some exes are not good candidates for the DD, and should be avoided.

The most successful DD’s end amicably, and often times with a friendship that was stronger than when it began. Sex with an ex should never be a tool for reconciliation, though -- it is a reward that comes after reconciliation -- way, way after.

Because I love you and also Children’s Literature, I’ve created a Choose-Your-Own-Adventure guide to the successful DD. here's hoping you don't fall into the volcano on your quest for erotic treasure! And watch for pirates! (Disclaimer: I would totally fuck a pirate. And also date one.)

The Fantastical Freedom Ride of [your name here].

We begin at the breakup.

Freshly plucked from your cozy love nest, the single world is a cold, lonely place. You're at a bar late night with friends who, in attempts to cheer you up, keep pointing to drunken slops as suggested rebounds. They're loud, charmless strangers who you couldn't imagine sharing a quickly melting twin popsicle with, let alone bodily fluids. Sex does sound good though, and like your best friend always says: The best way to get over someone is to get under someone else! But who...? Proceed to checkpoint 1.

1. Your ex crosses your mind. No, not that one, he's dating someone. Oh come on, you know which one. Proceed to number two.

2. Leaning on the bar, you wonder: Has enough time passed that you have both moved on and are at peace with the fact that your relationship is over? If yes, proceed to three! If not, go home and charge your vibrator.

3. Around closing time, IPhone in hand on the sidewalk, you consider: Have you both dated other people at least semi-seriously since the relationship ended? If yes, congratulations! You have likely gained some perspective, move ahead to 4! If not, proceed to 7, at the bottom of this article.

4. It’s been a while since last you talked, so you scan his Facebook: Has he or she recently ended something? If not, great! It's likely they are in a good place! If yes, their pride is hurting, and though its possible for this to work out, it is a bit riskier. You may end up looking like the answer to a problem. If you're going to move ahead, have the conversation about this FIRST, and then proceed to five. If you don't want to have the conversation, proceed to 8, at the bottom of this article.

5. With your finger on the send button, sexy text locked-and-loaded, you ask yourself: This guy was a good guy, right? While assholes are often excellent sex partners, their charm is fleeting, because being a nice human is more sustainably attractive. In all likelihood you respect yourself way more now than when you dated an asshole, and you'll be disappointed by how much less his "Rebel Without a Cause" shit works on your vagina. There are so many different ways to be an asshole that it’s impossible to create just one scenario of doom, but it’s not likely to end well. You’ll probably just be mad at yourself for ever being attracted to someone who is such a jerk. If you like being treated poorly by assholes, please proceed to number 10, at the bottom of this article.

6.The Sex was at least "good" the last time. Usually, it gets better during the DD, because it's the main event and doesn't come with a host of emotional vulnerabilities that may keep either of your mouths shut about what you want. If it was terrible to start with though, the margin for improvement is not unlimited, and you're better off exploring other avenues. Liked the sex? Just wait till you see what happens this time! If you choose to text an ex who was bad at the sex, please proceed to 9, at the end of this article.

If you made it to the bottom, get psyched! You're probably about to have a healthy DD! Sex is a human need. Just because you’re not into the idea of giving your heart to anyone at the moment, doesn’t mean you have to be celibate. I can't stress how important this last part is, though:

Establish rules before you jump in the sack. What does this new arrangement look like? What is the communication expectation? Any ambiguity is a chance for either of you to get hurt, since the idea of NSA sex, though awesome, goes against the social conditioning we’ve been fed our whole lives. You care about this person and visa versa, so: Keep it simple and friendly, and remember that even if you didn't use STD protection while in a relationship with this person, this is not the same situation. Wrap it up!

And don’t forget that when you do find someone you want to date again, your DD needn’t disappear from your life. Friends are friends, and the good ones are forever. So many of my exes are now my good friends, and the peace that comes from acceptance can reach you about yourself in invaluable ways -- Plus it makes the DD pool even bigger.

Happy Dippin’!


7. An evil goblin named Neveralone creeps up behind you and blindfolds you -- you can no longer see WHY you ever broke up with DD -- he makes you feel so loved! His addiction/infidelity/lack of intelligence/general incompatibility with your personality is just a hurdle, and you two can tackle it together! It will make you closer! YOU FAIL. THE END.

8. In bed post-bangin', you realize how swimmingly everything is going -- you almost can't believe how satisfying it is to have a purely sexual relationship. When you say this out loud, DD begins to weep, quietly. Guess you should have talked, huh? YOU LOSE YOUR FRIENDSHIP. THE END.

9. To say that the sex was disappointing would be mild: His version of oral felt like he was trying to give your vagina a “raspberry,” or maybe the intercourse was jackhammer/30 seconds long/strangely silent/unadventurous/fruitless for you/just plain boring. Panic sets in. What have you done? Shit, you could have had a V8! Sex with your ex was way better than this, have you made a terrible mistake? What if you NEVER HAVE GOOD SEX AGAIN? The post-breakup mind operates in extremes -- breaking up with someone takes bravery, which means you really want to know that you made the right call. This is why we often reject so many parts of our old life, trying to prove to ourselves that we’ve done the right thing. Any hiccup can make us irrationally question the end of something that really did need to be ended. BE STRONG, GAYLE. THE END.

10. Sitting on a bench in the lower East Side of New York City, you look to your right, and the woman beside you looks vaguely familiar. You glance at her lap and see the name Jackie Mancini on a pile of papers she’s scribbling on. Oh hey, you say. You write for xoJane! Yes, she says, and I’m writing an article right now about people who like being treated poorly by assholes. What’s the title, you ask. “[Your name] Should Really Invest in Therapy, Because He/She Deserves to be Treated Well, Regardless of the Situation.” Oh, you say. Then we hug. THE END.