He absolutely should. After fessing up to spending time with Rihanna, Tyra Banks and Kat Dennings, we think one of the following five ladies might be a decent match for Mr. “Hold On We’re Going Home”. But is he up for courting Chilli, and would he have chemistry with K.Michelle? Keep reading as we explore the matchmaking options, and take our POLL at the end!
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?
2. Aubrey Plaza
Aside from having the same first name (…think about it) we believe these two would make a magical comedic duo. Drizzy prides himself on being able to make his women of past and present giggle, and Aubrey’s proven love of sweaters means they’re already compatible.
So… the next time they both touch down in New York, Drake will take her out for lobsters and shrimp at the Oyster Bar in Grand Central (it’s not touristy, it’s classic) and then head to a late night show at the Upright Citizens Brigade. Plaza is a pro, but Drake’s improvisational and sketch comedy skills could use some work, so he’d be happy to sit in the audience–plus, he likes a woman who is confident in her abilities and popping off on her own. After the show, they’ll carouse with mutual friend Judd Apatow and the cast of his latest movie until the wee hours. Drake may or may not try too hard to make people laugh.
As we’ve gotten to know Aubrey Graham over the years, one thing is clear: he likes his women curvy. That, and he has a penchant for lady ratchetness (“She just want to smoke and f*ck/ I said ’girl that’s all that we do'”), so we’d like to imagine that K.Michelle might tickle his fancy.
Looks aside, she’s talented: that girl can sang! Yes, she’s currently tied to NBA player Lance Stephenson, but should that fall through, Drake would be the perfect rebound cushion to shower her in devotion. Her thick figure is Drake’s type to a T, and we can already hear the sultry duet produced by R. Kelly. Oh, and just in case their flame dwindles (K. might need a more gritty partner?), Drake could always rely on his busy schedule to keep the Love and Hip Hop Atlanta starlet on her toes. Sorta like this…
Frustrated, she waits for him after a gig with Henny on ice.
He arrives late. She’s mad, but she know she still cares for him.
You’ve seen this story before: They do whatever he likes.
4. Alex Morgan
At 24-years-old, this gold medal-winning member of the U.S. soccer team fulfills Drake’s longing for a female companion with an athletic build, while also helping to satisfy his current obsession with all things football.
Their date: an afternoon at the gym, followed by a pick-up game outside (shirts vs. skins, natch), a shower, and a cozy night at home playing FIFA. If all goes well, Drizzy will whisk her off to Spain where they can cheer on her favorite squad, FC Barcelona.
5. Zoe Kravitz
Since she’s grown up in the business with two famous parents, she’s looking for anything but a high-profile date night. Knowing this, Drizzy will take her to some dope thrift stores (she’s probably already been to) and get her opinion on new attire he won’t only be pulling out for Throwback Thursday. He’ll smile, she’ll nod, and 40 the rest of the OVO crew will suddenly get a flurry of texts claiming she’s “the one.”