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On the red carpet Rihanna was once asked by a reporter, “What do you look for in a man now?” to which the pop star famously responded, “I’m not looking for a man, let’s start there.” That single quote has long defined Rihanna’s approach to the male species and continues to empower men and women today. Of course, it hasn’t stopped the beauty and lingerie mogul to a colourful dating history (aka, the men that were never good enough for Rihanna).
This week the “Umbrella” artist announced her pregnancy with the one man that does seem to be good enough (at least for now), A$AP Rocky. Before we speculate on a due date let alone baby names, we’re revisiting some of Rihanna’s past relationships. And boy, this is a trip down the noughties memory lane.
Shia LaBeouf
This is one shouldn’t really count but it is too bizarre not to mention. According to the now-disgraced actor, LaBeouf and Rihanna went on one date around 2007. “[I was] filming a sword fight when I got the message [from Rihanna]. I said, ‘Can this be my life?’” he told Playboy at the time. They decided to meet in person. “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
Chris Brown
Chris Brown and Rihanna dated between 2007 and 2009. Brown was accused of physically assaulting the singer on their way home from a pre-Grammys party. He plead guilty to felony assault. The couple reunited in 2013 for a couple of months before breaking up for good.
Matt Kemp
The pop star dated the Miami Marlins baseball player between January and December 2010. “It was never as serious as it looked,” an insider told Us at the time. “It was always just [about] having fun.”
Karim Benzema
After an apparent hiatus from men, Rihanna was later linked to Karim Benzema. She met the Real Madrid soccer player at a nightclub in 2015. They were spotted dating a number of times before they reportedly split in 2017.
Lewis Hamilton
At the same time Rihanna was believed to be dating Benzema, she was seen getting very cosy with Formula 1 star Lewis Hamilton. They were seen vacationing together in the singer’s home of Barbados in August 2015 but it seems the pair split after a month.
Leonardo DiCaprio
Rihanna shared a short fling with the serial dater on Valentine’s Day in 2015 but it didn’t seem to go further than that. In 2016 the pair were seen kissing a New York City nightclub before reuniting at Coachella that same year.
Travis Scott
Long before Travis Scott was a baby daddy himself, he shared a short fling with Rihanna. They were seen kissing at a New York Fashion Week party in September 2015 in footage obtained by TMZ. Other than that, the rumoured romance was kept largely secret unfortunately for us.
drake
At the MTV Video Music Awards in August 2016, Drake seemingly confirmed his relationship with Rihanna after honouring the pop star in a speech, saying, she was “someone I’ve been in love with since I was 22.” Less than two months after the public display of love, a source told E! News that the couple split due to differing schedules.
Hassan Jameel
In June 2017, Rihanna and the Saudi businessman Hassan Jameel were spotted kissing while vacationing in Spain. At the time a source told Page Six, “This relationship is the real deal. Rihanna has told friends she’s in love with him and seems completely smitten. They’ve been spending a lot of time together away from prying eyes and are really serious. They’re really enjoying each other’s company.”
After three years of dating, the couple called it quits in January 2020. As for the reason, a source told People, “Their lives were too different, and it was hard to maintain a relationship.”
a$ap rOCKY
After months of rumours, it was confirmed that longtime friends A$AP Rocky and Rihanna were in fact dating in May 2021. In a GQ interview, the rapper told the publication that Rihanna was the “love of [his] life” and “the one.” They made their surprise red carpet debut at the Met Gala in September 2021.
The couple announced Rihanna’s pregnancy in January 2022.
