Rihanna doesn't just make hits; she makes history. But for a long time, her personal life felt like a puzzle that didn't quite fit together. From explosive pop-star romances to quiet flings with billionaires, the world has watched every move "Bad Gal Riri" made. Now that it’s 2026, and she’s settled into a life with three kids and a partner who treats her like the queen she is, looking back at who were all of Rihanna's boyfriends feels like reading a manual on how to eventually find "the one."
It wasn't always easy. Some of these guys were just passing through. Others left scars. But every single one of them led her to where she is now. Let’s get into the nitty-gritty of who actually held her heart—and who was just a rumor.
The Chris Brown Era: A Complicated Start
You can't talk about Rihanna’s dating history without mentioning Chris Brown. They were the "it" couple of the late 2000s. Two young stars at the absolute peak of their powers, seemingly unstoppable. They started dating around 2007. It looked like a fairytale until that 2009 pre-Grammy party incident that changed everything.
The physical assault by Brown was a massive cultural moment, and frankly, a traumatic one for her. They split, obviously. But the story didn't end there, which is what most people forget. They actually tried again. In 2012 and 2013, they rekindled things briefly. Rihanna told Vanity Fair years later that she thought she could change him. She realized she couldn't. It was a hard lesson in boundaries, and they finally called it quits for good in May 2013.
The Professional Athletes: Matt Kemp and the Sporty Side
After the first big split from Brown, Rihanna pivoted. Enter Matt Kemp. The Los Angeles Dodgers star was her "peace," as she told Elle magazine at the time. They were together from roughly January to December 2010.
Honestly, it seemed like a breath of fresh air. He was a pro athlete, she was a global icon, and they looked great together. But the "chaotic life" she lived (her words) eventually made things too difficult. They stayed friends, but the fire just went out.
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Then there were the rumors. You've heard them all.
- Karim Benzema: The soccer star was spotted with her in 2015. They were seen at nightclubs and late-night diners, but it never felt "official-official."
- Lewis Hamilton: Also in 2015, the F1 champ and Rih were seen getting cozy in Barbados.
The Drake Saga: More Than Just "Work"
Drake and Rihanna are the definition of "it's complicated." Their history spans nearly a decade. It started in 2009 with a date at a bowling alley and turned into years of collaborations like "What's My Name?" and "Work."
Drake was famously "in love with her since he was 22," as he announced to the world at the 2016 VMAs. They dated on and off, mostly off, for years. By 2018, the vibe had shifted. Rihanna told Vogue they didn't really have a friendship anymore. It was a classic case of two people who have great chemistry on camera but maybe don't click the same way behind closed doors.
The Billionaire Years: Hassan Jameel
If you want to know about the most serious relationship Rihanna had before her current one, you have to look at Hassan Jameel. This wasn't a "Hollywood" romance. Jameel is a Saudi businessman whose family owns the distribution rights for Toyota in Saudi Arabia.
They were together for three years, from 2017 to 2020. They were super private. No red carpets, very few paparazzi shots—just a quiet, serious love. Why did it end? Sources said their lives were just "too different." Rihanna was building an empire; he was running one. Sometimes, two worlds just don't align, no matter how much money or fame is involved.
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A$AP Rocky: The Slow Burn That Finally Stuck
And then there was Rocky. This is the part of the story that feels right. They were friends for years first. A$AP Rocky opened for her tour in 2013. They did the "Fashion Killa" video together. But the timing was never right.
Then came the 2020 pandemic.
While the rest of us were baking bread, Rihanna and Rocky were taking a road trip across America in a tour bus. That was the turning point. By 2021, Rocky was calling her "the One" in GQ. Since then, they've become a family of five.
- RZA: Their first son, born in 2022.
- Riot: Their second son, born in 2023.
- Rocki: Their daughter, who arrived in late 2025.
In early 2026, Rocky even opened up on the Popcast about how his mother, Renee Black, was the one who pushed him to pursue Rihanna years before he actually did. It turns out, moms really do know best.
The Lesser-Known Flings and Rumors
When people ask who were all of Rihanna's boyfriends, they often include names that were barely blips on the radar.
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- Travis Scott: They had a brief thing in 2015. He called her his "muse," but it didn't last long.
- Shia LaBeouf: He once admitted they went on one date in 2007. The spark? Non-existent.
- Leonardo DiCaprio: They were spotted together a few times in 2015 and 2016, but most insiders say they were just party pals.
What We Can Learn From Rih’s Journey
Rihanna’s dating history isn't just gossip; it’s a lesson in growth. She went from a toxic teenage romance to a stable, supportive partnership with a man she was friends with for a decade. She didn't settle. She tried different types—the athlete, the artist, the billionaire—until she found the one who actually fit her life.
If you’re looking to apply "Rihanna energy" to your own life, remember these three things:
- Friendship is the best foundation. She and Rocky were "just friends" for nearly eight years before they made the leap.
- Privacy is power. Her most stable relationships (Jameel and Rocky) were the ones she kept mostly away from the cameras.
- It’s okay to start over. Whether it was leaving Chris Brown or moving on from a billionaire, she never stayed in a situation that wasn't serving her anymore.
The road to 2026 wasn't a straight line for Rihanna, but looking at the family she’s built now, it’s clear she knew what she was doing all along.
To stay updated on the latest celebrity news and deep dives into Hollywood's most fascinating stars, make sure to follow reputable entertainment outlets that fact-check their sources. Real growth happens when you stop looking for the "perfect" partner and start looking for the one who grows with you.