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Rihanna’s relationship timeline: A roundup of all the guys the star has dated in the past

Rihanna broke the internet this week when she announced she’s pregnant with her first child. The star has been dating rapper ASAP Rocky for over a year and baby speculation for the pair has been swirling around for months. Just like the rest of the world, Rocky seems smitten with Rihanna, who recently referred to her as the “love of his life” in an interview for GQ.

Safe to say he’s not the only one to feel this way, as the singer has had a slew of other men fall head over heels for her in the past. From rapper Drake (who confessed his love for her on stage) and her most publicised relationship with Chris Brown, to soccer stars and F1 champions, here is a roundup of Riri’s past relationships and rumoured flings:

Chris Brown 2007 - 2013

Not long after she first came on the scene, Rihanna started dating Chris Brown. Both young and on the rise in their careers, the pair had an intense relationship filled with trust issues and insecurity, it was later revealed. Their issues culminated in 2009 when they got into an argument on their way home from a pre-Grammy’s party. Chris Brown physically assaulted Rihanna and was charged with a felony assault. However, the love was still there and they reunited briefly in 2013 before splitting for food just a few months later.

Image: @RollingOut/Twitter

Matt Kemp, 2010

After her first split from Chris Brown, Rihanna began dating baseball player Matt Kemp. They were first spotted together at a New Year’s Eve party in 2009 and then on a trip to Mexico in early 2010. However, the relationship was short-lived as by December 2010, the pair had split due to Riri’s busy schedule.

Image: @AaronGleeman/Twitter

Karim Benzema, 2015

While it was never officially confirmed, Rihanna was spotted with soccer player Karim Benzema multiple times in 2015. According to E! News, an insider said The Real Madrid star was a good match for Rihanna as they both had busy schedules and gave each other the space they needed. By 2017 however, the pair had reportedly split. A source revealed it was Rihanna’s unresolved feelings for Chris Brown that got in the way.

Image: @toptrevor/Twitter

Lewis Hamiltom, 2015

It seems Rihanna has a thing for men who are the top in their field. Also in 2015, Rihanna was spotted getting cosy with racing driver Lewis Hamilton. They were seen at a nightclub in New York City and then reportedly vacatioend together in her native Barbados. However, their fling ended soon after.

Image: @lewisgfreal/Twitter

Travis Scott, 2015

Later that year, Rihanna and Travis Scott were spotted getting cosy at a New York Fashion Week party in September. While the pair kept their relationship under wraps, Scott did describe Rihanna as his “muse” when asked about her in an interview.

Image: @infotrylie/Twitter

Leonardo Dicaprio, 2016

Another famous face on Rihanna’s list: Leonardo Dicaprio. The pair were spotted kissing in a nightclub in Paris, and then fueled further romance rumours when they attended Coachella together that following April. However, sources insisted they were “just friends.”

Image: @goslgns/Twitter

Drake, 2016

Who can forget the way Drake gushed over the star when he presented the Video Vanguard honour to her at the MTV Video Music Awards in 2016. “She’s someone I’ve been in love with since I was 22 years old,” he said, before attempting to kiss her in front of the world. Sadly, Rihanna swerved his advances on stage, and their relationship never materialised into anything public. Although the pair had collaborated on hit songs together, it seems they were “just friends”, according to a source. In January 2018 however, Rihanna told Vogue that she and Drake no longer had a friendship.

Image: ThePopTingzz/Twitter

Hassan Jameel, 2017

In 2017, Rihannas was spotted making out with Saudi businessman Hassan Jameel in Spain. According to her friends, this relationship was “the real deal,” and although they mostly kept their relationship out of the spotlight, the pair went on to date for the next three years. Despite the fact that Rihanna claimed she was “in love”, the pair called it quits in January 2020 due to the fact that “their lives were too different.”

Image: @envoguemag/Twitter

ASAP Rocky, 2020

Following her split from Jameel, Rihanna began spending time with long-time friend ASAP Rocky. He appeared in her Fenty Beauty campaign for men in August and by November 2020, the pair had officially gone public. In May 2021, Rocky called Rihanna “the one” and fast forward 7 months later, the couple revealed their baby news to the world in January 2022.

Eat your hearts out guys (and girls), Rihanna is officially off the market. We can’t wait to see the stylish couple be the dopest parents they can be.

Image: @PRADAXBBY/Twitter

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