We all saw the Instagram Drake posted after TLC’s Chilli jumped into his arms at OVO Fest. Aaliyah may have been his ’90s obsession, for when it comes to the music industry spotlight, Chilli was no small fry during that era. With the Sexy piece of CrazySexyCool, Drake’s childhood could nostalgia meet his older woman fetish in a magical way.
As we learned in What Chilli Wants when she dabbled in dating Floyd Mayweather, Chilli needs a lot of special attention. But who better than Drake? He’s a hopeless romantic searching for the right woman to not take advantage of his stardom. Already a veteran herself, Chilli could indulge in the dinners, trips, and gifts he’d bestow upon her, but not ruffle his famous feathers since she has her own re-emerging career with TLC’s album and film (The TLC Story) release next month.
Maybe closing the zoo for the day so that they can frolic with the animals might be a thoughtful date?