The pair dated briefly in 2009 after Rihanna split with Chris Brown - following his physical assault on her - and although Drake doesn't believe he was her "rebound guy", he admitted he thought there was more to the relationship than the 'California King Bed' hitmaker did.
He said: "I've probably been hurt more than I've hurt someone else. [With Rihanna, I wasn't] necessarily the rebound guy. At the time it hurt, but she didn't mean to. I'll never put that on her. I was hurt because I started to slowly understand what it was. I guess I thought it was more. That was the first girl with any fame that paid me any mind. You spend days reading about this person in the magazines. All of a sudden you have this number-one song and you're at some birthday party and there she is. And you're just some naive kid from Toronto staying in some shitty-ass hotel who got invited to this party on a whim. That's just how it happened."
Drake also revealed it is difficult to date because of his fame as women often find it difficult to trust him.
He added to American Elle magazine: "[It's hard] to get women to trust you. When you have a woman in your life and you're telling her, 'I'm in New York working on my album,' and you're actually in New York working on your album, but they're saying you're in the Bahamas with so-and-so, it's hard for her to believe. I've had women lash out based off the fact that they think I'm lying when I'm not."