How To Date Ex-Boyfriends

Sounds ridiculous, doesn’t it? Well, it’s as predictable as rain in Seattle. You’re going to encounter that man who breaks your heart numerous times, then you’ll find a technicality to justify your guilty displeasure.

If you describe him to a friend, and the sentence ends in one of the following, I’m talking to you.

  • … but the sex was so good.
  • … but he was great with my kids.
  • … but he always treated me nice when he was with me.
  • … but he says he has changed.
  • … but my friends and family love him.

OK, sugar, if you must go there, you must know the way. You don’t need any lectures from me about how past behavior is the most accurate predictor of future behavior, do you?

His infidelity will give you the irresistible urge to hack into his email, read his text messages, or stalk his Facebook activity. He knows this, so don’t waste your time. The best strategy on your part is to avoid dirt, instead of seeking it. Work on your “not giving a shit” attitude. Even if you fake it, you’ll be pleasantly surprised at the effect it has on him. Here’s a great line you can use to send him sideways:

“If you must do something stupid, do me a favor and don’t compound it by letting me find out about it.”

Let’s say you haven’t reconnected with him yet, but you seek advice on how to approach him. Fine. Here’s a typical scenario, and how you should proceed.

You were with Tom for many years. You had your ups and downs, like any relationship. He frequently hinted that he was ready to seal the deal (yes, put a ring on it), but never did. Just when you thought you saw that sparkling gem in the distance, it turned out to be the headlight of a speeding train about to splatter you across two counties. He went on a business trip, boinked some hosebag, and you found out. You booted his sorry ass to the curb.

A month later (and a few dozen roses), he begs you to take him back. You’ve gone on three horrible dates since his departure, and you’ve gone through both seasons of Orange is the New Black … twice. You deploy one or more of the aforementioned “buts,” and agree to meet him.

Now, first thing, Missy, is you’re not sleeping with him tonight. Don’t you fucking dare! Give yourself a few pre-meeting orgasms, if necessary, but grant him no access to your nethers. Break out your ho-i-est club attire—there must be excessive cleavage and neon straps. Have him meet you for dinner at Ruth’s Chris or a place likewise grossly overpriced. Order a bottle and go for the fine cuts. Watch him cringe as he signs the tab.

When he drives you home, do not invite him it. In fact, take his goodnight kiss on the cheek. Depart the passenger seat slowly, to give him a good sight of your delicious posterior. Repeat the date until there is sufficient remorsitude. Forgive. Then, don’t be surprised when he breaks your heart again.

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About the author

Author of humorous essays about relationships and lifestyles.