Fans of Rihanna’s have been eagerly anticipating her Super Bowl halftime show. The 2023 show would not be the first time she was headlining the event, but a lot has changed since her previous Super Bowl stint. She is now a mother and is in a steady romance, and her current status will likely prompt some fans to take a look at her past relationships. Who has Rihanna dated previously?
Rihanna Had an Intense Relationship With Chris Brown
Rihanna’s first serious romance was with fellow entertainer Chris Brown, noted Us Weekly. The two started dating in 2008, and they had been friends for some time prior to that. In February 2009, however, Brown was arrested after an incident that occurred the night of the Grammy Awards. CNN detailed that the two had a fight after he received a text from a woman after the awards show. “I caught him in a lie, and he wouldn’t tell the truth. And I wouldn’t drop it,” Rihanna told journalist Diane Sawyer. “It escalated into him being violent towards me. I was battered, I was bleeding, I was swollen in my face,” Rihanna explained.
Brown ultimately pleaded guilty and was sentenced to five years of probation, one year of domestic violence counseling, and six months of community service. Brown and Rihanna reunited romantically in 2012, but the relationship ended a few months later.
Rihanna Dated Drake Twice
After putting her time with Brown behind her, Rihanna was briefly linked to singer Drake and later dated baseball player Matt Kemp for about a year, detailed PopSugar. Romances with soccer star Karim Benzema (per Page Six), rapper Travis Scott, actors Leonardo DiCaprio and Ryan Phillippe, and race car driver Lewis Hamilton garnered attention for a while too. In early 2016, Rihanna reunited romantically with Drake.
Rihanna and Drake dated for much of 2016, and as he presented an award to her in August 2016, he noted, “She’s someone I’ve been in love with since I was 22 years old. She’s one of my best friends in the world.” After splitting with Drake in October 2016, Rihanna found herself in a romance with Hassan Jameel, a billionaire from Saudi Arabia. When asked by her “Ocean’s 8” co-star Sarah Paulson during a chat for Interview if she was in love, Rihanna replied, “Of course I am.” She played coy when asked about marriage, then added, “Only god knows that, girl.” When asked about becoming a mother, however, Rihanna admitted she wanted that “More than anything in life.”
In January 2020, People reported Jameel and Rihanna had split after dating for about three years. “Their lives were too different and it was hard to maintain a relationship,” a source told the outlet of the couple. There were engagement rumors swirling at one point, but the two never married.
Rihanna Almost Immediately Found Romance With A$AP Rocky
Almost immediately after splitting with Jameel, Rihanna was seen getting cozy with A$AP Rocky, shared The Sun. During the summer of 2021, Rocky told GQ Rihanna was “The love of my life.” The two had generated romance rumors in early 2013, but it wasn’t until early 2020 that Rihanna and Rocky really embraced a blossoming relationship. Rocky admitted being in a relationship was “So much better when you got the One,” and “I think when you know, you know. She’s the One.”
Rihanna and Rocky announced her pregnancy in January 2022, and their son arrived in May. The couple is still going strong, although so far, it doesn’t seem an engagement or wedding is in the immediate future for them.