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Super Bowl LVII: Rihanna's dating history has been mixed, from Chris Brown lows to A$AP Rocky highs

Rihanna has kept her relationships mostly private, but occasionally news about her partners has hit the headlines
PUBLISHED FEB 12, 2023
Rihanna has had a 'rocky' dating history from Chris Brown to ASAP Rocky (Frazer Harrison, Jesse Grant, Mike Coppola/Getty Images)
Rihanna has had a 'rocky' dating history from Chris Brown to ASAP Rocky (Frazer Harrison, Jesse Grant, Mike Coppola/Getty Images)

GLENDALE, ARIZONA: The Super Bowl LVII halftime show was one of the most iconic solo performances in history. Fans from all 32 teams joined forces to perform a unique rendition of one of her singles ahead of Rihanna, the multi-Grammy-winning singer's long-awaited return at Super Bowl LVII on Sunday, February 12. The Kansas City Chiefs and Philadelphia Eagles competed in a game that day.

Rihanna's appearance comes as the NFL begins the first year of its new partnership with Apple Music as the principal sponsor of the halftime show, replacing Pepsi. “We’re excited to partner with Rihanna, Roc Nation, and the N.F.L. to bring music and sports fans a momentous show,” said Oliver Schusser, Apple’s vice president for Apple Music and Beats. In addition, a once-in-a-generation artist, Rihanna took the center stage and was the star of the Super Bowl at the Arizona Cardinals State Farm Stadium.

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Rihanna and A$AP Rocky welcomed their first child together in 2022 and the couple are still going strong. The new parents attended their first Golden Globes in January 2023, where Rihanna was nominated for best original song, 'Lift Me Up', from 'Black Panther: Wakanda Forever'. Therefore, it's safe to assume that both Rihanna and A$AP Rocky have 'Love on the Brain' at the moment. However, not all of RiRi's past relationships were this good.

How did Rihanna and Rocky meet?

Throughout her career, the superstar has kept most of her relationships private, although occasionally news about the partners Rihanna has had, made headlines. Some fans were startled by her current relationship with A$AP Rocky given that the two had been close friends for a long time, as reported by The Things.

Although there are contradictory accounts of how Rihanna and A$AP Rocky first met, all of them point to the same year — 2012. Rocky's appeared on the remix of Rihanna's song 'Cockiness (Love It)' while Rihanna played the love interest in Rocky's Fashion Killa music video. Both these collabs are cited as their first-ever interactions but neither of them has clarified this point, so we will never know till they spill the beans.

The couple has been frequently seen out together, going on outings and even extended vacations together, ever since People reported their relationship in November 2020. Later on, People reported on May 19, 2022, that Rihanna and A$AP Rocky had given birth to their first child together.

Who all did Rihanna dated before A$AP Rocky?

Many would contend that Rihanna felt A$AP Rocky was deserving of being the father of her child given that she had previously dated a number of A-list celebrities.

Drake and Rihanna

Drake attends Drake's Till Death Do Us Part rap battle on October 30, 2021 in Long Beach, California.
Drake (Photo by Amy Sussman/Getty Images)

In 2016, when they appeared at each other's concerts, Rihanna and Drake created their own relationship rumors. At the MTV Video Music Awards that August, the 'Hotline Bling' rapper declared that Rihanna was "someone I've been in love with since I was 22", in a heartfelt acceptance speech for the Video Vanguard award. The pair, who have worked together on songs including "Work" and "Take Care," showed up at a VMA afterparty "looking very much like a couple and extremely in love," according to sources. 

A source informed E! News less than two months later that Rihanna and Drake had split due to scheduling conflicts but were "still in each other's lives" as close friends.

Chris Brown and Rihanna

Chris Brown performs onstage during
Chris Brown (Kevin Winter/Getty Images for Radio.com)

In 2005, Chris Brown and Rihanna were both budding musicians when they first came together. But their relationship didn't begin until 2007. When it was discovered that Brown had physically assaulted Rihanna on their way home from a pre-Grammy party, the couple had a sensational breakup in February 2009. The 'Look at Me Now' singer pleaded guilty to felony assault and finished probation, community service, and therapy for domestic violence in March 2015.

Early in 2013, Brown and Rihanna made a brief reconciliation. At the time, the 'Love the Way You Lie' singer told Rolling Stone, "I realized it was more essential for me to be happy. Even if I made a mistake, it was my fault. However, they had permanently broken up by April of that year.

Matt Kemp and Rihanna

Singers Rihanna and Matt Kemp outfileder of the Los Angeles Dodgers baseball team attend Cleveland Caveliers and  Los Angeles Clippers NBA basketball game at Staples Center on January 16, 2010 in Los Angeles, California. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement.
Singer Rihanna and Matt Kemp, outfielder of the Los Angeles Dodgers, attend Cleveland Cavaliers and Los Angeles Clippers NBA basketball game at Staples Center on January 16, 2010, in Los Angeles, California(Kevork Djansezian/Getty Images)

After her initial breakup with Brown, Rihanna started dating MLB player Matt Kemp. After being photographed together on New Year's Eve in 2009 and subsequently on a vacation to Mexico at the beginning of 2010, the couple ignited dating rumors. The ex-LA Dodgers outfielder exclaimed to Us Weekly in May 2010: “Yeah! That’s my girl! She’s just a fun person. I love to be around her.” They split up in December 2010 due to the singer's hectic schedule.

Karim Benzema and Rihanna

Karim Benzema receives the Ballon d'Or award during the Ballon D'Or ceremony at Theatre Du Chatelet In Paris on October 17, 2022 in Paris, France.
Karim Benzema (Aurelien Meunier/Getty Images)

Rihanna has also been linked to soccer player Karim Benzema. She allegedly met the Real Madrid player in a nightclub, and the two were then pictured together at a restaurant in New York in June 2015. In July of that year, Benzema was a wonderful fit for the 'Diamonds' singer because he understood her rigorous schedule and offered her "the space she needs", an insider told E! News.

In 2017, the couple officially called it quits. A source close to Benzema revealed the separation to the Spanish magazine Don Balon Rosa, saying, "Rihanna liked Karim, and she had a lot of fun with him. [But] She said that she will always love Chris Brown but assured him that she did not wish to hurt his feelings."

Lewis Hamilton and Rihanna

Lewis Hamilton of Great Britain and Mercedes talks in a press conference during previews ahead of the F1 Grand Prix of Abu Dhabi at Yas Marina Circuit on November 17, 2022 in Abu Dhabi, United Arab Emirates.
Lewis Hamilton (Rudy Carezzevoli/Getty Images)

It appears like Benzema and Rihanna were not exclusive because the 'Where Have You Been' singer was sighted vacationing with Formula One driver Lewis Hamilton in her native Barbados in August 2015. A Page Six spy then spotted the couple getting "cozy" at New York City's 1 Oak nightclub, but their relationship terminated soon after.

Hassan Jameel and Rihanna

Hassan Jameel (Hassan Jameel/Twitter)
Hassan Jameel (Hassan Jameel/Twitter)

Rihanna dated Saudi businessman Hassan Jameel for almost three years before splitting up in 2020. "This relationship is the real deal," an insider remarked during their crazy affair. Rihanna has admitted to friends that she is head over heels in love with him. Hassan was said to have even met Riri's mother. 

Who are the men Rihanna has been rumored to have an affair with?

Leonardo Dicaprio and Rihanna

Singer Rihanna and actor Leonardo DiCaprio attend the Levi's Brand and RE/DONE Levi's presents NEON CARNIVAL with Tequila Don Julio on April 16, 2016 in Thermal, California.
Singer Rihanna and actor Leonardo DiCaprio attend the Levi's Brand and RE/DONE Levi's presents NEON CARNIVAL with Tequila Don Julio on April 16, 2016, in Thermal, California (Jesse Grant/Getty Images for Best Events)

Rihanna and Leonardo Dicaprio were reportedly seen kissing in a Paris nightclub in January 2016, according to Page Six, despite claims on the contrary from insiders close to the duo at the time. When the A-listers were spotted hanging out together at Coachella that April, romance suspicions about them intensified even further.

Travis Scott and Rihanna

Kanye West, Travis Scott and Rihanna attend Vogue 95th Anniversary Party on October 3, 2015 in Paris, France.
Kanye West, Travis Scott, and Rihanna attend Vogue 95th Anniversary Party on October 3, 2015 in Paris, France

A month after Lewis Hamilton, Rihanna was photographed with another renowned face, Travis Scott. In September 2015, TMZ received a video of the 'Work' singer and the 'Sicko Mode' rapper kissing at a New York Fashion Week party. They kept their romance private, but when the singer was asked about it later that year, Scott urged the journalist not to "do [me] like that, man". He then described her in three words, "creative," "inspiring," and "muse," as reported by Page Six.

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