Should You Date Your Ex?

When you start dating someone new, there are few words that can express those first passionate kisses, playful touches and glances, and feelings of pure lust. But what if your someone new is, in fact, someone old; a repeat offender, if you will? When you choose to do a re-do with an ex, the complications become exponential. But, like my mom always said, ‘Anything can be pretty,’ which I think means that there is a good side to everything. So, as someone who is contemplating a re-do, I had to think about the positives and the negatives.

The biggest negative is obviously that you broke up for a reason, and nine times out of ten, those reasons are still present. As my ever-optimistic friend puts it, “Boys will always have dicks and will always be dicks.” I firmly believe that people can tweak their behavior, but no one can really change in a major way, because it is simply too difficult. So those small annoying habits and major deal breakers will still be there.

Without fail, shit fails apart; it always ends in the end. Either due to death or break-up. Negative #2 is when your end was not ended with the words, “We just didn’t work out, but I really hope he/she is happy.” I’m sorry, this is not Girl Scout camp, and no one really wants their ex-anyone to be happier with someone else. But, when your relationship ended because of, let’s say, ‘extracurricular activities,’ the hard feelings are like rocks. But, when you have dated someone for any considerable length of time, they sort of date your friends and family, also. So, the issue is how do you bring your oldie to any friend or family function without your concerned bestie or sister mumbling, “I can’t believe she took him back”?

Clearly a positive is sex. Not to be a total ball of testosterone, but let’s face it: when you start dating someone you’ve already slept with, it eliminates the awkward, ‘I want to sleep with you, but I don’t want to look like a skank-ho tramp’ inner monologue you have with yourself. Not only do you not have to wait for the sex, it will be good. Hooking up with people for the first couple of times is awkward because everyone has their own personal technique, and sometimes synchronizing two techniques is as awkward as walking your dog without pants on. But if you are doing it with someone who knows you, then it is effortless and naturally wonderful. And, as an added bonus, if the break-up was bad, the first two months of sex will alternate between ‘angry, I still hate you sex,’ and make-up sex.

Another positive is that you really know this person. Since you two have already broken up once before, you have seen him at his very worst. There are no pretensions or unknowns and you know exactly what kind of dance you are stepping back into.

Breaking up is hard to do, but re-kindling with an ex is even harder, because there is more at stake. There are emotional investments, which means that if it falls apart again, get ready to listen to depressing music, buy stock in Hershey’s chocolate, and possibly buy an extra copy of “The Notebook” because yours might break due to repeat watching.

If getting back together with an ex is something you are seriously considering doing, then there is really only one question to ask yourself: “is it worth the possible and probable shit that will ensue?” If the answer is yes, then good luck, and if it is no, then break out those short dresses, because you are going trolling for men.