Can Casual Sex Turn Into Something More?

Sex 911: Confessions of a Serial Dater

Sometimes I think I would've been happier growing up in the 50s. Sure I wouldn't have had things like an iPod, boxer briefs, or Portillo's hot dogs, but life would've definitely been simpler.

Something I know I would've loved is a 1950s relationship. They were simple. You were either dating someone or you weren't, period. Today, there are too many kinds of relationships out there. It's confusing. There's exclusive relationships, friends with benefits, booty calls, one-nighters, and everything in between.

As puzzling as these relationships may be, there's nothing wrong with any of them, if that's your thing. What's more perplexing is trying to figure out what comes first -- the relationship and then sex, or sex and then a relationship? It's like the chicken and the egg theory. You'll pull your hair out trying to think of an answer.

You hear it all the time, people saying that if you have sex too soon, it dooms the relationship. But is that really true? Can a serious relationship blossom out of a sexual one?

Many believe that a friendship can grow into love. You might even know an annoying couple like this. You know the ones I'm talking about. They tell their sappy "When Harry Met Sally"-type story to anyone who'll listen. It's disgusting. You get a cavity just hearing it.

As nauseated as they make you, they do prove a good point. If they can build a relationship from friendship, then certainly you can build one from sex, right? I know this is true because I could've done it myself -- only I blew it.

I'm talking a gal from my past who we'll call Nicole. Nicole and I've been close friends for almost 10 years. We met through friends, and eventually started messin' around.

It started out as the classic booty call scenario. She'd call me at 2 a.m. to see if I wanted company or I'd invite her over. We both knew what the relationship was, and it was a lot of fun. Then the party came to a screeching halt.

Nicole said she wanted something more than just sex, but I tend to avoid serious relationships the same way I avoid John Mayer songs. I wanted no part of it. At the time the only thing I thought I was losing was good sex with a fun girl. No biggie.

After a few months of not talking, we started hanging out again, and of course, having sex. On the surface it seemed like she was having sex with me in hopes that I'd change my mind and take that giant leap into relationship-dom, but she gave no hint of that. Soon after we were finished having sex she'd say, "Well, I gotta go." Normally that would be most guys' dream, right? Wrong. Something weird happened.

She told me about this new guy she was dating, and I never heard her rave about a dude this way before. I started getting a weird feeling in my stomach. Ruling out food poisoning or a tapeworm, I concluded that this is what jealousy must feel like.

After some thought, I told her I was now ready to get serious. Uh huh, you guessed it. It was too late. She chose the other guy because I was too much of a crapshoot and he was a sure thing. She knew my take on relationships and decided I was too risky. It was like an ironic Greek tragedy. She's now married to him with three kids. We still talk and get together occasionally, but of course no hanky panky.

OK, dry your eyes. It's not that bad. There's a valuable lesson to be learned here, which is yes, serious relationships can indeed come from sexual relationships. But unlike me, it can only happen if you're willing to take the next step. So if at any time you begin to feel something stronger for your booty call, take a chance and just go for it. Sure you might freak them out which may end the sex, but when they find someone else, it's going to end anyway.

Imagine all the "woulda, coulda, shouldas" you'll save yourself.

Learn more about Jon at and on the Better Sex page.

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