nAUGHTy Girl Chronicles. Vol 6.

Diary entries of a Black girl navigating love, lust, and the aughts in D.C.

April 2009

[Song that played at the speakeasy]

Dear Diary,

He looked up from staring straight at my breasts and said, “Oh, I’m sorry. What did you say?”

That’s when it hit me. I was sitting there in my brand-new $168 dress, $100 hair-do, $50 in fresh MAC makeup, $40 mani-pedi, $15 cab ride, and hours of prep for this date that turned out to be an expensive lesson.

Back in 2006, when I first met him, he gave off that whole “renaissance man” vibe. Confident but not too cocky, well-traveled, sharp, funny. The type of man who could make you feel like you’d leveled up just by being near him. I was intrigued.

Fast forward to this year. I get this random GChat message out of nowhere. “You? Online dating? No way you need that.” I laughed. He was referencing my GChat status that read: “Dating apps are the absolute worst.” Same old smooth talker. We started chatting again, casual, harmless, slightly flirty. I mentioned I was working on my grad school statement, and he offered to help. Given his whole Yale-Rhodes Scholarship-world-traveler-author résumé, I figured, why not? He actually made the statement better, so when he said he’d be in town for business, it felt like a nice full-circle moment. I said yes to drinks.

We met at this new speakeasy uptown that needed a password to get in. Cozy place, dim lights, real moody. I looked amazing. He looked… okay. Maybe a 7 on a generous day. Gaps across multiple teeth, hairline fighting for its life, and this smug grin that told me his ego had been eating protein and working out since the last time I saw him.

Ten minutes in, I wanted to leave. Every conversation turned sexual. I asked him about his career. He told me about his “wild time” in Brazil. I wanted to talk about going to grad school. He brought up our “chemistry.” I said I was struggling to make new friends. He asked if I’d at least been getting laid. He bragged about flying his exes out for “casual fun.” I just kept sipping my drink and counting down to the moment I could leave without it being awkward.

Then he switched gears. “So,” he said, “You went to Chicago to work for the Obama campaign. Did you ever get to meet him?” I said no, already bracing myself for the flex I knew was coming. Sure enough, he smirked. “I mean, my father hosted a fundraiser for him. So, yeah, I’ve met him a few times.”

I nearly rolled my eyes right out of my head. He was dripping in arrogance, thinking that would make my pussy drip. I realized right then that this man didn’t want a date. He wanted to collect another pussy stamp on his little global conquest card.

But he didn’t know who he was dealing with.

Years in this city will teach you plenty about men who look good on paper, but ain’t shit in real life. I’ve dated them all: the broke dreamers, the fake hipsters, the self-proclaimed rebels, the wannabe intellectuals. I thought this one would finally be someone on my level. Turns out, the only thing he had more of than passport stamps was ego.

Somewhere between his bragging about sleeping with women all over Latin America during his gap year and explaining “levels of prestige” in the legal world, I realized something. He wasn’t testing me. I was testing myself, seeing if I’d still fall for the same type of man who mistakes arrogance for depth.

The old me probably would’ve. But not tonight.

I leaned back, looked at him in those self-satisfied blue eyes, and said, “Thanks for the drink. I’m gonna head home.”

It wasn’t just self-control. It was growth. I know what I’m worth. No degree, no passport, no Yale pedigree can compete with that.