Rihanna Dating History: Exes, Flings, Romantic Relationships

Lucky guys! Rihanna‘s relationship history is filled with an interesting mix of men. Her romance with billionaire Hassan Jameel ended in January 2020 after three years, and she has since moved on with rapper A$AP Rocky. However, these are far from the only A-list bachelors in her dating history. From Drake to Chris Brown and even Travis Scott — the singer has had a few surprising names pop up in her romantic past.

She and Hassan were first linked after the two were spotted making out in a hot tub back in 2017. They managed to keep their relationship relatively low-key, but the “Stay” artist admitted “of course” she was in love during a sitdown with actress for magazine in June 2019. Sadly, they broke things off less than a year later.

The billionaires really seemed to connect, and a source exclusively dished to Life & Style that they were even thinking of taking another big step in their relationship. “I know for a fact that she would love to be a mom. She can’t wait to have kids. In fact, she wants a daughter first,” a source close to the Grammy winner disclosed at the time.

There was just one more milestone her Saudi boyfriend wanted to hit before starting a family. “Her boyfriend, Hassan, definitely wants to be married first,” the source added about the possibility of RiRi having a baby.

Although many celebrities try to keep their pregnancies under wraps as long as possible, the insider teased that the “Umbrella” artist won’t keep fans guessing. “When she does finally decide to have a child, she says you’ll see more than just a little bump because she won’t even try hiding it. She’ll embrace it,” they divulged.

Details are still fuzzy on why the couple ended things, but Rihanna seems happier than ever with A$AP. A source told Life & Style in December 2020 that Ri and the “Fashion Killa” artist “have a ton in common, besides music.”

“They’re creative, very family-oriented, they make each other laugh — and the best part was that they were friends first, which helps. It’s the basis for a great romantic relationship,” explained the source.

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The pair welcomed their first child together, a son, in May 2022. Six months later, a source told Life & Style exclusively that the A-list parents want to have more kids.

“Rihanna loves being a mom and she loves seeing A$AP’s daddy side,” the insider revealed at the time. “She just sits back and beams watching them together. Seeing father and son bond just melts her heart.”

Keep scrolling to see Rihanna’s impressive list of past loves!

A$AP Rocky

Rihanna and A$AP have fueled dating rumors off-and-on for years. They collaborated on her single “Cockiness (Love It)” in 2012 and he joined her tour as an opening act the following year. They attended events together through the years as friends, but in 2020, things seemingly took a romantic turn.

The pair are still going strong and welcomed their first child together in May 2022.

Drake

Will they or won’t they? From 2009 to 2016, Drake and Rihanna had rumors swirling about their possible on-again, off-again romance. They have worked on music like “What’s My Name?” and “Too Good” together, but first sparked interest when they were seen making out at a bowling alley in 2009.

Although the Barbados babe has always insisted that they’re just ~good pals,~ Drake told Ellen DeGeneres in 2013 that they dated.

In 2016, it seemed like they were back on. They got matching tattoos and the rapper gave a very sappy speech while presenting Rihanna with the Michael Jackson Video Vanguard Award at the MTV VMAs. However, it was reported that they split seemingly for good in October 2016.

Leonardo DiCaprio

Rihanna and Leo heated up back in January 2015 when the two got cozy on the dance floor during her 27th birthday party. They were then seen smooching at a nightclub in Paris a few weeks later. The duo was also spotted at Coachella together in April 2016 but seemingly went their separate ways afterward.

Chris Brown

This was perhaps one of Rihanna’s most publicized relationships … for negative reasons. The two seemed perfect for each other when their romance was confirmed in 2008. In 2009, Chris was charged with two felonies after physically assaulting her. Surprisingly, the two got back together for a stint before ending things for good.

Rihanna explained why she reconciled with Chris during an interview with Vanity Fair in 2015. “If you put up with it, maybe you are agreeing that you [deserve] this, and that’s when I finally had to say, ‘Uh-oh, I was stupid thinking I was built for this.’ Sometimes you just have to walk away,” she said.

Matt Kemp

The baseball player — who also had a brief fling with Khloé Kardashian — dated the songstress for almost a year in 2010. They seemed absolutely smitten for each other. “I’m so happy. I feel really comfortable, and it’s so easy. [The relationship] is just my peace. It keeps me sane,” Rihanna said about Matt at the time.

Things fizzled out because the Fenty founder needed to focus on herself. ” 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,” she explained to Vogue in 2011.

Shia LaBeouf

The actor and Rihanna raised some eyebrows when they were spotted out to dinner together during the summer of 2007. Two years later, Shia cleared the air about their night out during an interview with Playboy.

“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,” he explained. Surprising but OK.