Drake's 10 Hottest Hook-Ups

When: May 2010

Drake turned the pole-dancing stripper chick into video vixen when he casted her in his video for "Find Your Love." It was well-known that the two were hooking up when a slew of pictures of the Canadian rapper and the booty model lounging at a nightclub surfaced on the Internet. He also gave her a shoutout in "Miss Me." In June 2010, Maliah told VIBE that she had met Drake's mother. Bringing a stripper to meet your parents? Is that a smart idea?

Smash Probability: Yeah, this happened.

When: May 2009

All it took was a Photo Booth picture of Drake attempting to lip-lock with Teyana Taylor for the "Are they a couple?" rumor mill to start rolling. The images were uploaded by the Harlem-born rapper/singer on her MySpace page. Though nothing was confirmed, a picture is worth a thousand words. In this case, four pictures.

Smash Probability: They were cuddle buddies at the very least.

When: August 2011

After being snapped hitting a Florida resort to play tennis together, Drake was rumored to be doing a little something-something with tennis star Serena Williams. Drake was also spotted cheering on Serena when she played (and won) the 2011 Rogers Cup in the rapper's hometown of Toronto. Then a clip of Serena twerking it to Trey Songz's "Bottoms Up" in Drake's condo surfaced. Grand Slam winner turned video vixen? Drake would later deny and say that it was not his place.

Smash Probability: She definitely helped him practice some type of stroke.

When: November 2011

Earlier this month, Taraji revealed that Drake tried to hook up with her. The 41-year-old actress went on the record and said that Drake is just "a friend" and said that if he were 10 years older, she would have been down. She then went on to compare Drizzy's age to that of her son. Bummer.

Smash Probability: We're willing to bet that Drake will hold her to those comments next decade.

When: January 2009

Drake named his critically acclaimed So Far Gone track "Bria's Interlude" as a tribute to the model and video vixen. In an interview where Drake broke down each track from the 2009 mixtape, he described the song saying, "I was smitten over this girl from L.A. and I started writing a song about her." Ms. Myles is in fact from Los Angeles. As for if the two actually hooked up, Drake proclaims, "A lot of the R&B [I do] is really based off women that come into my life and inspire me to speak to them in song and say what I never would expose on just a talking level.”

Smash Probability: We'll never think this guy couldn't pull any video girl he's "smitten" with.

When: October 2011

After announcing her split with her long-term boyfriend of nearly five years, Nicole and Drizzy were spotted leaving an Italian eatery in L.A. (separately) late last month. The X-Factor judge then took to Twitter to say, "Wow, now anyone that happens to be in the same restaurant is linked to me." Drake also denied that he was dating the Pussycat Dolls singer in a recent radio interview. Ms. Scherzinger is still however single and ready to mingle.

Smash Probability: It wouldn't have been surprising if she was looking for a rebound, though.

When: Unknown

In our cover story earlier this week, Drake claims that he only admired Quincy Jones' daughter from afar. "I was, like, in love with Rashida. I love funny women and I love beautiful women and I love women that have great taste in music and Rashida is all those things," he said. They met when she complimented his DJ set at a party, and coincidentally linked at a later date when they stayed at the same resort on vacation. Maybe they had that Black Jew connection, but Rashida is famously low key, and we know Drake would respect that.

Smash Probability: What happens on vacation stays on vacation.

When: 2009

If you've heard "Look What You've Done" off Drake's newly released Take Care, he raps about his ex-girlfriend Zineb Samir—better known as Nebby Neb. Drake even appeared on Toronto's FLOW 93.5 to answer the questions on who "Best I Ever Had" was about and revealed that the song was for Nebby. We can definitely see why.

Smash Probability: Rapping about making a girl's special place "whistle" is confirmation enough.

When: January 2011

From hoping they'd get married on "Miss Me" to an actual Twitter matrimony, Drake proclaims his love for his Young Money labelmate constantly. The two were reported as "dating" when they were spotted late last year at a New Year's Eve party in Miami "dancing and cuddling." It's hard to say if the rumors of romance between the two are actually real, but according to Drizzy, Nicki definitely "makes him proud." Whatever that means.

Smash Probability: This is like one of those office romances that neither party can admit to.

When: May 2009-August 2010

Drake and Rihanna have definitely hooked up. They were spotted in Toronto late last summer eating at one of his favorite restaurants, spotted bowling at Lucky Strike in New York City the month before Thank Me Later dropped, and spotted again at a Montreal nightclub during Rihanna's LOUD tour. These two have chemistry, both on record and on-stage. Drake describes the relationship as a "natural bond." People love to call him a "simp" for doing things like wearing a T-shirt with her face on it, but son, you'd simp on RiRi too if you had the chance.

Smash Probability: He could tell it wasn't love, he just thought she fucked with him.