Casual Dating Doesn't Work for Everybody, Especially Me

casual datingI’m coming up on an anniversary worth being acknowledged, maybe even celebrated with ice cream cake (for what is a celebration without the delectable goodness of cake-form ice cream?). All to cheer on my recovery from being a fool. Once upon a time, I was in a really ugly place that had me plotting, planning, and pleading for a man I loved to love me back.

Mind you, it wasn’t supposed to be that way in the first place. My crazy tail flipped out over the dude who was designated as The Rebound Guy.

He was just supposed to be the man who helped me get my sea legs in the dating world after my boyfriend of eight years — eight long, engagement ring-less years — forced me to put a toe tag and time of death on our marathon relationship. After spending most of my 20s booed up with dead weight, I was understandably a bit disillusioned with love and happily ever after.


So there I was, fresh out on the market, pumped full of encouragement and advice from my homegirls, instructed to play the field, revel in my singleness, and treat them suckas like hoes. That last one was the gem from my college roommate, who’s never without a bag of boys to pick and choose from. So I figured maybe she was on to something in her emotional detachment from her he-harem of male playthings.

For as long as I could remember, I’d always had a man. It certainly hadn’t been anything intentional — I’m definitely not one of those chicks who needs to have a guy in her life. It just happened that way. But it also meant I’d skipped the chapter of The Womanhood Experience where you go out on casual dates. When a guy I’d known in passing from college starting flirting with me heavy on Facebook, he seemed like as good a place as any to brandish my new, unfettered attitude towards relationships.

Random status comments turned into steady inbox messaging, which spilled into texts and eventual phone calls until we met for the first time in a public area with plenty of escape routes in case one or both of us felt shortchanged by misrepresentative profile pics. Instead, our chemistry was crazy. We debated about social issues, talked about hip-hop, laughed at weird-looking passersby. He admitted it was the best date he’d ever been on. I was convinced that if this was what dating was like, I’d be A-OK.

The last thing on my mind was snagging myself a new man. I knew that. My brain knew that. But my heart ain’t listen. Without that heads up, it didn’t just fall in love. It somersaulted into it. Problem was, my Facebook Crush didn’t want a girlfriend. And remember now: I was charged with being footloose and fancy-free my doggone self. But as a handful of dates turned into regular hangouts, I started to wonder why he didn’t want me when a swift kick of common sense should’ve told me that, if I ever had to ask myself that question, I needed to be thankful that he didn’t.

I’m pretty sure now in retrospect that I was trying my best to force my vision of how perfect we’d be together on him. He wasn’t catching it, but that didn’t stop me from selling it. In the meantime, he was reaping the benefits of my infatuation. I hang my head in shame to admit how many times I hopped in my faithful hoopty to drive from my apartment in D.C. to his place in Philly just because he said he wanted to see me. On top of wasting gas money and precious hours of sleep schlepping up and down I-95 like an interstate trucker, I compromised my self-esteem and my heart by dragging out the inevitable.

Every woman eventually gets to a point where being stuck on stupid gets old. My a-ha moment took longer than it should’ve to arrive. Hear him tell it, it came right as he was about to make that commitment. Of course now, when I look back, I’m fully aware that he was ultimately doing me a favor by not booing me up.

The best revenge now is bumping into him and being my normal, sweet self. I know he regrets stringing me along because he told me as much. I appreciate his honesty. But more important than his Confessions of an Apologetic Would-Be Ex is my own regret for offering myself up to be treated like an option instead of a necessity.

Have you ever tried to turn a jump-off situation into something more? How’d that work out for you?

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