Rihanna’s Romantic History: Chris Brown, Drake, A$AP Rocky & More – Hollywood Life

Rihanna’s Romantic History: From Chris Brown To Her Second Baby With A$AP Rocky & More

Rihanna's love life has been in the headlines for nearly two decades. From her tumultuous relationship with Chris Brown to her second baby with A$AP Rocky, look back at who Rihanna dated.

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  • Rihanna’s exes include Drake and Chris Brown.
  • She’s currently dating A$AP Rocky.
  • Rihanna and A$AP welcomed their first child together in May 2022.
  • Rihanna announced her second pregnancy at the 2023 Super Bowl Halftime Show

Ever since she burst onto the music scene in the early 2000s, the world has wanted to know more about Rihanna‘s personal life. The Anti singer, 34, has been romantically linked to plenty of high-profile men, and fans are certainly familiar with some of her most notable boyfriends including Drake and Hassan Jameel. RiRi is currently dating superstar A$AP Rocky, whom she welcomed her first child with on May 13, 2022. Rihanna revealed her second pregnancy with A$AP while performing at the 2023 Super Bowl Halftime Show on February 12, 2023. Read on to find out more about Rihanna’s love life.

Chris Brown

Rihanna and Chris Brown cozy up courtside at a basketball game. Image: SplashNews

Rihanna and Chris Brown were one of the most infamous couples of the late noughties. The pair of hitmakers, who burst onto the scene in the 2000s with chart-toppers like “Pon de Replay” and “Run It,” respectively, were just teenagers when they made it big. They duo had their ups and downs over the course of their tumultuous relationship. The 2009 incident in which Chris physically assaulted Rihanna has come to define not only their relationship, but Chris’ career. On the day of the 2009 Grammys, it was announced that the pair, who were slated to perform together, would not take the stage. Chris had brutally beaten Rihanna the night before, leaving her with a busted lip, black eyes and multiple bruises.

Much to the surprise of fans, RiRi forgave Chris several years later. The pair rekindled their romance in 2012, and she spoke to Oprah Winfrey about the relationship during an episode of Oprah’s SuperSoul Conversations. During the conversation, she said that Chris was her “true love,” and said that she considers him the “love of [her] life.” She added, “We’ve built a trust again, and that’s it. We love each other and we probably always will. That’s not anything that we’re going to try to change. That’s not something you can shut off if you’ve ever been in love.” During the brief period they were back together, the pair were spotted sitting court side at basketball games and getting cozy on vacations together. They split for good in 2013.


Drake professes his love to Rihanna at the 2016 VMAs. Image: AP Images

Rihanna and Canadian hitmaker Drake were friends and collaborators before they ever dated. The pair met in 2005 while she was shooting a music video in Toronto, but they didn’t go on their first date until 2019. They dropped a number of collabs through the years, including “Work,” “Take Care,” and “What’s My Name” and were believed to have had an on again/off again relationship which persisted until 2016. RiRi told Vogue in 2018 that things had gone sour between the former couple, and they were no longer friends. “We don’t have a friendship now, but we’re not enemies either. It is what it is,” she said at the time.

Matt Kemp

Rihanna and Matt Kemp enjoy a basketball game. Image: AP Images

The “Wild Thoughts” singer dated LA Dodgers star Matt Kemp for the better part of 2010. During their relationship, Rihanna told Elle, “I’m so happy. I feel really comfortable, and it’s so easy. [The relationship] is just my peace. It keeps me sane.” Nevertheless, she split from the baseball player that December and went on to open up about the relationship four months later, in Vogue, saying, “I just let it go. I don’t ever want to have to depend on a relationship. I think it’s a really special thing to find love. It’s beautiful. Nothing can match it, but I want to make sure I find other things in life that I love — besides love.”

Leonardo DiCaprio

Rihanna and Leonardo DiCaprio are rumored to have dated. Image: AP Images

Back in January 2015, rumors began to emerge that RiRi was dating Hollywood A-lister Leonardo DiCaprio. He attended her 27th birthday party, and they spent Valentine’s Day together in 2015. The following year they were spotted together sporadically, at a club in Paris and at Coachella. And in 2017, the Oscar-winner was caught sneaking into the after party for her Fenty x Puma runway show!

Travis Scott

Rihanna and Travis Scott quietly dated before he got with Kylie Jenner. Image: AP Images

Rihanna dated Kylie Jenners future baby daddy Travis Scott back in 2015. The former couple were first spotted together at New York Fashion Week and it was quickly reported that the pair were “officially” together. Nevertheless, the relationship was short lived, but he did go on to serve as the opening act on her 2016 Anti World Tour — so it seems there’s no bad blood!

Hassan Jameel

Rihanna and Hassan Jameel kept their three-year relationship private. Image: BACKGRID

Perhaps RiRi’s longest and most stable relationship was with Middle Eastern businessman Hassan Jameel. They dated for three years, but were famously private and hardly ever made public appearances together. She spoke multiple times about how happy and in love the pair were, including in Vogue in late 2019, when she said, “I’m actually in an exclusive relationship for quite some time, and it’s going really well, so I’m happy.” Thus, it came as a surprise to fans that she called it quits with the billionaire in January 2020. Given the secretive nature of their relationship, little is known about why they split.

A$AP Rocky

Rihanna and A$AP Rocky walk the red carpet at the 2019 Fashion Awards. Image: AP Images

Rihanna and buddy A$AP Rocky, 34, were romantically linked in early 2020 after being spotted hanging out just days after her split from Hassan. The twosome flamed the romantic spark throughout the year, especially after being seen getting awfully cozy on a dinner date in November, just days after Thanksgiving. She even brought him home to Barbados for the holidays, where they packed on the PDA, even holding hands during a stroll on Christmas Eve.

A source told HollywoodLife EXCLUSIVELY that Rihanna wants A$AP to be her “final boyfriend” — she’s that happy! “Rihanna has dealt with it all, from good to great to bad relationships. The way things are strolling along is looking very special,” they said. “Ri is really all about A$AP. Things are just amazing right now. She is in very bright spirits.”

Rihanna & A$AP Rocky share a passionate kiss while hanging out at Barcade in New York City. It was a rare showing of PDA for the couple. (Richard/Cesar/TheBigShotApp/Shutterstock)

Rihanna and A$AP confirmed that they’re expecting their first child together with a series of photos where the singer showed off a baby bump on January 31. The pair were holding hands on a snowy day, as Rihanna sweetly had her stomach poking out from under a hot pink coat. This will be the first child for both the singer and rapper! Besides the baby on the way, wedding bells may come soon! A source close to the pair told HollywoodLife EXCLUSIVELY in January 2022 that it was “only a matter of time before [A$AP Rocky] proposes.”

In April 2022, A$AP was arrested at LAX Airport after vacationing in Barbados with a pregnant Rihanna. He was taken out of the terminal in handcuffs by authorities. A$AP’s arrest was reportedly in connection to a November 2021 shooting, where the rapper allegedly fired a handgun during an argument with an acquaintance. The victim sustained minor injury from the incident and later sought medical treatment, according to NBC News. A$AP was identified as the alleged shooter by the LAPD.

Despite the arrest, the couple remained as close as ever, and welcomed their son together on May 13, 2022. The baby boy, whose name is yet to be revealed, is the first child for both parents. Nine months later, Rihanna revealed her second pregnancy at the Super Bowl Halftime Show. She rocked a head-to-toe red ensemble that showed off her baby bump during the performance. Ri’s rep confirmed that she’s expecting her second child, per The Hollywood Reporter, after the performance.