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And while I can’t imagine being with my Cuba date “for real”—I mean, he’s a low-key homeless anarchist who once took me on date to his Sex and Love Addicts Anonymous meeting; there are red flags—I still value our relationship immensely.

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After four years, scads of lays, and many great girlfriends (plus plenty of failures along the way), he launched this website.

"After he left, I was suddenly repulsed — not by his penis, but by his personality and the night as a whole.

And I actively avoid his texts and calls to this day."2. You better take that into consideration before getting it on with someone you can't imagine your life without.

On the other hand, when the reality of how your sex buddy spends his time away from you—and vice versa—sets in, that geographic proximity could very well be the downfall of your casual relationship, says Rachel Russo, a dating, relationship, and image coach based in New York City.

In a few days, I’m going to Cuba on vacation with a guy I’ve been sleeping with for eight years, but whom I've never once called my boyfriend.

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