A #Woke Dude's Dating Diary

Bumble (her): Do you want to go out?

(Me): No, I want to stay in the virtual world of Bumble and date you. You are hotter on BUMBLE than real life.

(Her): That's not true.

(Me): Prove it.

FOUR HOURS LATER:

We are kissing on a sidewalk somewhere near Chicago’s St. Patty’s green river when I feel her hair extensions. Plastic braces weave into her scalp, and my hand is sliding up and down trying to figure out what it is exactly. I’m drunk, I realize. She stops kissing me and lets go of my hand.

What the fuck was that?

“Joe, can we go to 7–11? I need to get something,” she asks.

Should I say something? Is she embarrassed? I’ve never kissed a woman that has hair extensions. Why would she have hair extensions, her hair seems just fine?

“What, do we need condoms?” I chuckle sarcastically, lying about what I really want to ask her.

“A bit presumptuous big man,” she says, grabbing my hand again.

“Sabrina, I’m not going to have sex with you tonight,” I say. “It’s just not how I roll.”

She rolls her eyes and starts walking, her knee-high boots clicking the sidewalk. And truth be whispered, I don’t always like to have sex with strangers, but, shhhh, I try to be transparent about any hookup that may be waiting in the stars. Hell, I was a virgin until I was 25 and 13 years later, I am still learning what women mean when they say something, when their body language changes.

Yeah, I know, I missed out on a lot of good sex, but after five good years of slut-ing the streets of Europe and breaking up with a woman I dated and loved for six years, I knew one thing about my impending sexual revolution:

Good sex was (usually) intimate, passionate, and fun. The kind of sex where you can relax and breathe and laugh and trust the process; where you can get lost exploring skin and scent and pull some goddamn hair without worry of a goddamn hair extension coming with it.
Maybe I am just an atypical male. Or is it possible more men need to talk about being single and 38 so I can feel better about my lack of intimate sex? Oh, while I’m ranting, the other problem with one night stands is I always feel like I’m trying to act out a porn scene, which doesn’t align with my number one principle in life:

Be fucking authentic. If it feels intuitively wrong, try not to do it.
Says the guy that fails at that constantly. Intuition is hard to corner when you aren’t present (or when you are drunk). And to be honest, one of my biggest fears is having sex and making babies with someone I’d never be with in real life. Maybe I lack self-confidence. Or I’m just dealing with the conditioning of a society where other guys have fantastic sex on their one night stands, and I don’t.

Conceivably, that’s it: I’m just jealous of those dudes.

Regardless, it doesn’t matter, I try the best I can to live with my principles, listen to my intuition, and ignore people that don’t like all my shiny green feathers and weird idiosyncrasies (fuck their burn, with love).

Sabrina appears at the 7–11 cash register with a bottle of red wine and a pack of Marlboros in her hand. Something dawns on me, something that always happens too late on a first date:

Beauty is no real measure of a woman’s worth and our society can condition us to have fucked up values, which can make authentic dating a shit show.