This Saturday, Drake is scheduled to remind the world that yes, he can act, as he takes on both musical act and hosting duties for Saturday Night Live. As his dating life has been a major influence on his music (think of all the past loves he’s name checked in his tracks), we’re thinking that emotional side of him will be used as inspiration for some pretty funny skits. All of this had us thinking about all the women that Drake has tried to make his boo-thang since he stepped in the spotlight, and the list includes quite a few famous ladies. These folks decided to kiss and tell:
Sumpter has said in the past that she had a “little crush” on the rapper, but in an interview with Necole Bitchie, Sumpter said that before he made it big in music, they went on a date.
“That was one date. The whole cast [of Nickelodeon’s Best Friend’s Date] went out to dinner. He was so nice. And I remember him being like, ‘I’m working on music,’ and he sent me some music, actually. So yeah, he’s been working on music for a long time. And I just remember- I used to call him Aubrey. And he was just super sweet and super nice.”
We all know that it was this little lady who played a part in Drake trying to exchange bottles (like…through the air) with Chris Brown, and he admitted that he talked about their relationship in the song “Fireworks” from Thank Me Later:
“I could tell it wasn’t love/ I just thought you f—ed with me/ Who could have predicted/ Lucky Strike would have you stuck with me…Damn, I kept my wits about me, luckily/ What happened between us that night it always seems to trouble me/ Now all of a sudden, these gossip rags want to cover me/ And you making it seem like it happened that way because of me/But I was curious and I’ll never forget it baby/What an experience, you coulda been the one/But it wasn’t that serious, there was smoke in the air before before that was me clearing it/That felt good…”
Despite the age difference (she’s now 39, he’s 27), Drizzy told Ellen that he went on a date to Disneyland with the woman behind America’s Next Top Model and the former Sports Illustrated cover girl:
“I went on a date with her one time, yeah. We went to Disneyland in disguise actually, which was fun. I don’t know if it was a date. It was a get together. We’re close as well.”
Drake had his eye on the 2 Broke Girls star for a while, and said that one day she finally gave in and went on a date with him. Unfortunately for Drake, Dennings didn’t call him back after the fact:
“I just always had a huge crush on Kat Dennings and she was kind enough one night to oblige me and we went out for dinner. They don’t call me back after one date according to this.”
The rumors are swirling that Kravitz and Drake are a couple now, but if they aren’t, they’re some very cozy friends. Drizzy reportedly has showed up at her shows with her band, they’ve been seen kissing at Beyonce’s Mrs. Carter World Tour show in Philly, and she’s been seen hopping out of his private jet and on to his tour bus recently.
Who could forget this beauty, originally a King of Diamonds stripper who was featured as the love interest in Drake’s “Find Your Love” video. The two were in a relationship that lasted a short time, but Michel claimed he wasn’t fond of her stripping for a living and things ended from there:
“Honestly, from what I heard it was ….it’s always this way with dancing and that’s why it’s so hard for dancers to take relationships seriously because everything is fine when it just fun but once the guy starts to really care about you, oh, it’s his friends. “You don’t understand her career” but it’s like ‘I don’t know, do you think you should be going this far?” People get in their ear; it never fails. It can be a regular Joe on the street or an entertainer.
As dancers we always get slack once the guy starts to care about you and want to take things a step further.”
It’s unclear how things went between Serena and Drake, but the rapper gushed over the tennis star when speaking to Complex:
“I really, really love and care for Serena Williams. She’s incredible. That’s someone I’m proud to say I know. She’s definitely in my life and I’m in her life. It’s great to watch her play tennis. Very impressive.”
This same love and care for her didn’t make the rapper Common too happy, as the two ended up in a very weird and thankfully short-lived rap beef.
Were they or weren’t they? That was the question last year. All this came up after the two were snapped together on her birthday at Supperclub late last year. Ali finally tried to clear up the rumors that they were more than friends, but spent a majority of her interviews playing coy:
“He is absolutely brilliant. And I am a huge fan of his…I wasn’t popping bottles like that, but he got me a beautiful bottle of champagne and it fell down from the sky and I felt really special.”
Drizzy also mentioned her in his song “Tuscan Leather,” off the new album, Nothing Was The Same:
“The fresh prince, just had dinner with Tatyana, no lie/All these 90’s fantasies on my mind/The difference is that with mine, they all come true in due time”
Model Bria Myles had quite the effect on Drake, as he mentioned her in at least two songs: “Bria’s Interlude,” and a song from his recent album, “From Time.” He recounted in the ladder of meeting her in Houston:
“Now it’s therapeutic blowing money in the Galleria/Or Beverly Center Macy’s where I discovered Bria/Landmarks of the muses that inspired the music/When I could tell it was sincere without tryna prove it”
Video model Dollicia Bryan’s reps confirmed back in 2011 that she and Drake were an item. The pictures of them canoodling in the club definitely made that clear. But just as quick as they were together, they were finished. There were rumors that they fell out over homeboy wearing colored contacts…but that sounds pretty ridiculous so we’ll just say they realized they weren’t really all that compatible.