Drake Shares His ‘Personal Feelings’ After His 2 Exes Performed With Kendrick Lamar at the Super Bowl

SZA (2009)

Drake confirmed that he dated SZA when he dropped the song “Mr. Right Now” in October 2, 2020 where he rapped, “Yeah, said she wanna f–k to some SZA, wait / ‘Cause I used to date SZA back in ’08.” SZA responded to the claims on X (formerly Twitter) two days later. “So It was actually 2009 lol 🙃.. in this case a year of poetic rap license mattered 🥴 lol I think he jus innocently rhymed 08 w wait . Anybody who really knows me and was around during this time can confirm.. it’s all love all peace 🤝💎💫”

She continued the thread, “I just didn’t want anybody thinking anything underage or creepy was happening. Completely innocent. Lifetimes ago.”

She doubled down on it in an interview with Rolling Stone, saying they were “were really young.” “It wasn’t hot and heavy or anything. It was like youth vibes. It was so childish.”

Recently, two of SZA’s co-stars grilled her about her relationship with Drake. In a Hot Ones Versus episode to promote their movie One of Them Days, Keke Palmer asked the “All the Stars” singer if Drake was a good singer. SZA kept mum for the most part. “We were children!” she exclaimed. “We were children. 2009? We were children.” For her part, SZA was really joking—Drake was 23 years old at the time and SZA was 20 years old. Palmer and Issa Rae fanned the flames saying that her answer would be a “simple good or not good,” with Rae adding it was “really easy.” The Insecure creator continued, “And the fact that you don’t want to say one is very telling.”

Kat Dennings (2011)

Drake went on a single date with Two Broke Girls star Kat Dennings after thirsting over him on the Twitter Timeline. “Kat Dennings I just woke up out of bed to let you know you were a dime on Conan tonight. XO,” he tweeted on May 10, 2011. He’s been open with his crush on Dennings when he told Ellen DeGeneres, “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.”

Dennings revealed that Drake did in fact take her out in an interview with Chelsea Handler. “We had sushi — we were being followed by a black SUV with his security,” she said. “It was overwhelming the amount of security.”

Serena Williams (2011)

Drake briefly dated Serena Williams in 2011. He made a nod that his single “Too Good” was written for her. “I get heavy on a couple joints, but this is more about me and Serena,” Drake said of the track during a studio session, which featured Rihanna and was included on his fourth studio album, Views.

“It’s funny because when I make songs about women, I also make songs for them. So, I know what kind of song to make,” he continued. “If I’m gonna talk about them, I’ll at least do them the justice of making them a song that they like. So, I know Serena very well and I know that she’ll hear it loud and clear, but she’ll also not hate me for it because it’s lighthearted.”

In 2025, Serena Williams danced alongside Kendrick Lamar when he headlined Super Bowl LIX and performed the hit Drake diss track “Not Like Us.”

Rihanna (2009 – ?)

Drake and Rhianna had quite an expansive relationship. The two were in an on-and-off relationship for 10 years. The two met when Drake was an extra in the music video for her song “Pon De Replay. ” In 2009, Page Six reported that Drake and Rihanna were seen kissing at a restaurant in New York City after her breakup with Chris Brown. “She was drinking whiskey and apple juice and making out with him all night,” a source told the site at the time. In an interview with Vanity Fair in 2015, Rihanna denied that she ever dated Drake and confirmed that her last “official” boyfriend at the time was Brown. Rihanna also told Vogue in 2018 that she and Drake weren’t friends anymore. “We don’t have a friendship now, but we’re not enemies either. It is what it is,” she said.

Hailey Bieber (2016)

Drake briefly had a fling with Hailey Bieber (then Hailey Baldwin). “Drake and Hailey are dating super casually, but he is really into her,” an insider told People. “They met through mutual friends and are taking things slow.” The two quickly called things off.

Jennifer Lopez (2017)

After a photo emerged of the “Let’s Get Louder” and Certified Lover Boy cuddling together, the two seemed to hit things off for a limited time. “It was never very serious. They like one another and had fun together,” a source told People said at the time. “It was and is fun when they see each other. They love hanging out and making music together. [Jennifer] has great respect for him and his talent and he does for her as well.”

Sophie Brussaux (2017)

Drake’s rep denied that Sophie Brussaux was carrying his baby in 2017. However after a paternity test proved that Drake was indeed the father, Drake started to support his son Adonis. He claimed that he and Brussaux were never in a relationship in his song “March 14” from his album Scorpion, rapping, “She’s not my lover like Billie Jean but the kid is mine/Sandi used to tell me all it takes is one time, and it took was one time/S—, we only met two times, two times.”

Julia Fox (2020)

Julia Fox and Drake had an interesting fling in 2020. In a February 2022 episode of her Forbidden Fruits podcast, she clarified that they didn’t properly date. “He’s a great guy and a gentleman … and that was it. Nothing really happened, we were just, like, friends hanging out,” Fox said. “I wouldn’t say that we were dating.”

However in an episode on Watch What Happens Live With Andy Cohen, she revealed that her date with Drake was one of her best dates.  She said, “being on a private jet, cuddled on the jet, landed, got some Chanel bags … it was great, yeah.”

Johanna Leia (2022)

Drake dated the mom of Amari Bailey, Johanna Leia in the summer of 2022.  ABC7’s helicopter spotted Drake and Leia having dinner near the first base line after the rapper made a donation to a Dodgers’ foundation.