Relationships Archive

When a Lifelong Scrub (Finally) Gets the Girls

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 …