Must be love on the brain! Rihanna’s dating life is as glamorous as ever. With her new baby and gushing over her BF A$AP Rocky, Rihanna has had quite the dating history.

From reported flings with Leonardo DiCaprio, to her on-and-off relationships with Drake, Rihanna still keeps mystery to her private life. On her type in men, she told The New York Times, “I’m turned on by guys who are cultured. That’ll keep me intrigued. They don’t have to have a single degree, but they should speak other languages or know things about other parts of the world or history or certain artists or musicians. I like to be taught. I like to sit on that side of the table.”

So who has Rihanna dated? Read more below to find out.

Who is Rihanna dating?

A$AP Rocky (2020 – present)

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A$AP and Rihanna met in 2012 after A$AP was featured on Rihanna’s song, “Cockiness (Love It).” They remained friends for years—A$AP even opened for Rihanna’s Diamonds World Tour in 2013—before news broke of their romantic relationship in January 2020, just weeks after Rihanna’s split from her then-boyfriend, entrepreneur Hassan Jameel. Rihanna and A$AP confirmed their relationship in December 2020 after they were photographed holding hands while walking around New York City.

Rihanna and her boyfriend A$AP Rocky announced her pregnancy in a photoshoot in Harlem, New York City in early 2022. In a surprise picture, Rihanna wore a long puffer jacket and exposed her very pregnant belly. In an interview with Vogue, she expressed how much A$AP supported her during the pregnancy. “What I love the most about us? Transparency with everything: how we’re feeling, what our goals are, what our fears and insecurities are. The vulnerability to be able to say what you feel about each other.”

In an interview with Zane Lowe on Apple Music 1 radio, A$AP Rocky was elated about his partner’s return to music. “I’m so glad that my lady’s back making music again and whatnot, and getting back out there,” Rocky told Apple Music. “It’s just incredible.” He continued, “The Super Bowl is huge, and her being the creative she is, she going to bring it, man. I’m excited. I’m more excited than everybody else, honestly.” According to VegasInsider’s polls, Britney Spears is the most searched guest appearance with Rihanna in the Super Bowl, followed by Eminem and A$AP Rocky.

After keeping her baby away from the public eye for seven months, the “Love on the Brain” singer posted a gentle video of the baby for her first TikTok with the caption, “Hacked.” “You trying to get mommy’s phone? Oh wow…oh wow,” she asked him after exclaiming “Ooh!”

Jameel Hassan (2017 – 2020)

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Rihanna was first linked to Jameel, the son of a successful Saudi Arabian businessman, in June 2017. She opened up about the romance for the first time in June 2019 when she admitted that she was “of course” in love with her then-beau. She also confessed that she would like to be married one day but doesn’t know when. “Only God knows that, girl,” she said. “We plan and God laughs, right?”

A source told Us Weekly in September 2019 that Rihanna and Jameel’s relationship worked so well because of their differences. “Rihanna and Hassan understand each other very well and their personalities mesh well together,” the insider said. “They’re both so different, but it works for them.” The two called it quits in 2020. 

Lewis Hamilton (2017)

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Though not reportedly official, Rihanna was rumored to date F1 superstar Lewis Hamilton. The two were spotted on a yacht getting cozy together in 2017. However the racecar driver denied the reports by calling the Savage X Fenty founder a good friend  “You know, I’ve known Ri for a long time, we’ve been friends for a while. We get to hang out every now and again…” he told E! News. 

Karim Benzema (2015 – 2017)

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Rihanna was linked to Karim Benzema from 2015 to 2017. The CEO and the Real Madrid footballer met at a nightclub and were shortly spotted at a dinner date in New York in June 2015. The pair were reportedly on and off throughout the two years but finally called it quits in 2017.

A source close to Karim told Don Balon: “Rihanna loved Karim, and with him she had a lot of fun. But she told him she did not want to break his heart, and she confessed that she’ll always love Chris Brown.

Leonardo DiCaprio (2015)

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Leonardo DiCaprio was rumored to have dated Rihanna back in 2015. The two were seen together in multiple instances like at Coachella. However, their fling was never confirmed by the singer or the actor.

Travis Scott (2015)

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Rihanna and Travis Scott fueled dating rumors after TMZ reported that the two were spotted making out in a New York City club in 2015. When asked about the Ocean’s 8 actress in his Complex cover story later that year, he told the interviewer to not “do [me] like that, man.” Then, when asked to describe her in three words, he said “creative,” “inspiring” and “muse.”

Drake (2009 – ?)

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Drake and Rihanna have had an interesting relationship. The two were first linked in 2009 and had several eyebrow-raising moments together throughout the years. 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.

Rihanna also told Vogue in 2018 that she and the Certified Lover Boy weren’t friends anymore. “We don’t have a friendship now, but we’re not enemies either. It is what it is,” she said. 

Matt Kemp (2009 – 2010)

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Rihanna briefly dated baseball player Matt Kemp from 2009 to 2010. When asked about the “Love the Way You Lie” singer, the former Dodger player told Us Weekly, “Yeah! That’s my girl!” He continued, “She’s just a fun person. I love to be around her.”

Rihanna called it quits with the athlete in 2010. An insider told Us, “It happened over the last few weeks,” explained the source. “She basically was just over it.”

Chris Brown (2007 – 2013)

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Rihanna and Chris dated on and off from 2007 to 2013. The two met early on in their careers with the two being photographed together in 2005. Their paths crossed again when Chris made a remix of her song “Umbrella” in 2019 and the two started to date shortly after. They appeared cozy together at the 2008 Grammys. 

In February 2009, Rihanna obtained a restraining order against Chris after he physically assaulted her before the 2009 Grammy Awards. The two had been dating for almost two years at the time of the assault. In February 2011, Rihanna agreed to drop the restraining order and she and Chris reunited in 2012 only to split a year later in 2013. In her interview with Oprah, Rihanna confirmed that the rumors of her and Chris’ recent reunion in St. Tropez were true. “We went to a mutual friend’s party on a yacht,” she said. “It’s awkward because I still love him. My stomach drops. I have to maintain this poker face and not let it get to the outer part of me. I have to maintain that and suppress it and interpret it and understand it and understand that it’s not going to go away. That is peaceful. If you don’t understand those feelings, you can make a lot of mistakes.”

Rihanna called Chris the “love of her life” in a conversation with Oprah Winfrey in Oprah’s Supersoul Conversation in 2019. “He’s in a relationship of his own,” Rihanna said. “I’m single. But we have maintained a very close friendship ever since the restraining order’s been dropped. We’ve just worked on it little by little. It has not been easy.”

If you or someone you know is experiencing domestic violence, help is available. Call the National Domestic Violence Hotline at 800-799-SAFE (7233) for confidential support.

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