In the early spring of 2016, I went out on a few dates with a woman named Jessica* whom I’d met on Match.
Jessica hit all the marks on the Jack & Jill checklist: preternaturally attractive, high-paying corporate gig, a condo in the South Loop (Chicago’s Mecca for well-heeled, bougie black folks); a fit frame, keen sartorial sensibilities and at least one NBA player on her roster. She was kind and gracious toward me – always comporting herself like the grown-ass woman she is.
I was still financially adjusting to being on my own after years in a two-income household, so I punched above my weight in dating her. When she insisted I accompany her for her routine massage at a parlor on the swanky Magnificent Mile where they charge you an extra $30 just for breathing their spa air, I had to do some mental gymnastics like ol’ girl in the meme before breaking out the plastic.
I’ve never truly believed in leagues considering how often I see gut-bucket niggas with fat wallets, The Best Personality Ever™ or a combination of both snag high-ranking women. But it wasn’t so long ago that I wouldn’t have even stepped at the line to take my shot with Jessica: throughout most of my 20s, I lacked the confidence and constitution to believe I could occupy the same air as a universally fine-ass woman.
My history of apprehension with the fairer sex is borne of my own “shortcomings” as a child: I was bony, short, translucent (relative to all the other black kids) and saddled with my mama’s jawline, which meant that my cheeks still make my face look like a Nick Jr. character. I attended two Detroit Public Schools where athleticism and “style” reigned supreme; I had no propensity toward maneuvering inflatable balls and any money I got my hands on was most likely going toward a video game, not shirts that had RALPH ELLIS, TOMMY HILFIGER and POLO splashed across them so goddamn hugely that I could help land a jumbo jet.
Shit really went pear-shaped for me when I hit puberty in junior high and grew a stomach and an extra chin or two, aided in no small part by my affinity for chili-cheese fries from the neighborhood Coney Island. On my first day of high school in the late summer of 1995, I was a pudgy little fucker who wore a charming little Mickey Mouse tie-dye shirt, for which I got roasted so badly I considered setting a match to it.
Never did I have the notion that a vagina-possessing human being would in any way romantically interested in me, so I didn’t have the grapes to approach them in the conventional sense. In contrast, Deh’ron, one of my closest friends, would spit game at anyone with a vagina – any digits I pulled as a teenager were only because he was close by. Of course, I had elevated standards, so my interests were the girls who were roundly unattainable to a scrub like me – my biggest crush was so fine that all the poop-butt niggas who also didn’t have a shot would bully me to get closer to her, on some “I’ll deal with this scrub for you” shit. (Oddly enough, she’s still a smoke show nearly 30 years later).
I fared only slightly better in college: I had a bit more courage, but not nearly enough to have engaged in the bacchanalia that everyone at least pretends to have in college. I only slept with two women in the entirety of undergrad – the woman I lost my virginity to at 19 and my first true love. What would’ve been my first sexual experience was courtesy of a mildly intoxicated women in my dorm room who asked outright, “Do you want a blowjob?” I responded, “Err, uhh, I mean, uhh…I never had one, sooo…” I walked away with Gobi Desert penis.
My ability to approach women with confidence didn’t truly come together until my early 20s, when I broke up with my college sweetheart and moved to Chicago. Even then, it was like when they gave Donald Trump the keys to the Oval Office: I didn’t quite know what the fuck to do with it. A decade ago, I had a sex/relationship column in a major Chicago newspaper at a time when I really had no business proffering anything resembling advice to anyone.
But even at 37 and with sensibilities that are markedly disparate from the ones I had a decade or so ago, that comic-book-reading, video-game-obsessed, bench-riding, off-brand-gear-wearing, skinny-fat Dustin bubbles somewhere just below the surface, informing everything I do. While I can intellectually acknowledge that I now have the CV to date women that a lot of niggas can’t pull (part of it might be the fact that I actually like women and am not a misogynistic roach), I’m still humbled when an attractive woman with options decides to take up with a wretch like me.
As for Jessica, my fate was likely sealed when I dropped her off one night, went in for the kiss and she gave me the Cheek of Death. She later explained to me that she was physically attracted to me but not sexually attracted, which befuddled the fuck out of me until I realized I feel the same way about Angela Bassett. Like, I simply have no interest in smashing America’s favorite mom this side of Jenifer Lewis, no matter how good she looks in a bikini at age fucking 60.
Jessica was completely gracious about breaking off the dating thing, leaving me with nothing but good things to say about her. But she also reminded me that I haven’t come so far from that 11-year-old scrub.
Which is probably a good thing. Staying humble has served me well.
*She’s literally the only person I’ve ever seen with her real first name. I won’t do her like that.