Rihanna Ex-Boyfriend: If you’re curious about Rihanna’s romantic past, you’re in for a treat. Rihanna and A$AP Rocky have been setting the music scene on fire as one of its most talked-about couples.
They kept things under wraps for a while before making it official in May 2021, and since then, they’ve been practically inseparable.
In fact, A$AP Rocky has publicly declared Rihanna as “the one” and “the love of my life” in a 2021 cover story of GQ, adding even more fuel to their already blazing romance.
Plus, they welcomed their first baby boy together in May 2022 and their second child in August 2023, cementing their bond even further. But before A$AP Rocky, Rihanna’s love life has been anything but dull.
From her highly publicized relationships with stars like Drake and Chris Brown to the more under-the-radar flings, she’s definitely had her fair share of high-profile romances.
So, if you’re curious about who else has caught the attention of this iconic singer, stick around because we’re about to dive into her dating history and ex-boyfriends over the years.
Rihanna’s Ex-Boyfriends: Every Man She Has Dated in The Past!
Let’s uncover the intriguing journey of love and heartbreak that has shaped Rihanna’s personal life.
Chris Brown
Rihanna’s first public relationship was with singer Chris Brown. They met as teenagers in the early stages of their music careers and collaborated on music, including a remix of Rihanna’s hit song “Umbrella” called “Cinderella.”
The pair were frequently seen together at events, like the Grammy Awards afterparty and Rihanna’s 20th birthday party, where Brown sang to her.
However, their relationship took a dark turn in February 2009 when Brown assaulted Rihanna in a car hours before they were scheduled to perform at the Grammys. Rihanna called 911 and Brown was arrested on felony charges.
Despite ups and downs, they briefly reconciled in 2012 but ultimately broke up for good in April 2013.
Drake
Rihanna and Drake had quite the rollercoaster romance from 2009 to 2016, marked by their catchy collaborations like ‘Work’, ‘What’s My Name’, and ‘Take Care’.
Their chemistry wasn’t just in the studio; it spilled over into the spotlight, keeping fans guessing about the status of their relationship.
But like many high-profile couples, they hit some rough patches. Rihanna even opened up to Vogue in 2018, revealing that their friendship had fizzled out, saying:
“We don’t have a friendship now, but we’re not enemies either. It is what it is.”
However, it seems time and maybe a bit of maturity have a way of healing wounds. Despite the ups and downs, they’ve found a way to keep things amicable.
Case in point: Rihanna showed up at Drake’s 33rd birthday bash in October 2019, suggesting that they’ve managed to patch things up, at least on a friendly level.
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Matt Kemp
Back in 2010, after Rihanna parted ways with Chris Brown, she found herself in a relationship with professional baseball player Matt for almost a year, from January to December.
Matt, who plays for the Miami Marlins, unfortunately, decided to call it quits with the Savage X Fenty star. The reason? Well, it seems Rihanna’s hectic schedule became a bit overwhelming for him.
According to a source who spilled the beans to US Weekly, Matt felt like he was constantly playing catch-up with Rihanna’s jet-setting lifestyle.
He was looking for something a bit more low-key, a bit more… normal. So, despite their connection, it seems the timing and lifestyle differences just didn’t quite align for these two.
Travis Scott
Back in 2015, Rihanna and Travis Scott sparked some serious dating rumors. They were spotted together at New York Fashion Week, and sources were quick to dish out the details to E! Online, saying things were getting pretty serious between them.
Travis seemed totally smitten with Rihanna, and it seemed like they were officially an item. But as quickly as it started, their romance hit a roadblock. It was reported that things became a bit too much for Rihanna, and their relationship fizzled out not long after it began.
Despite the initial buzz, it just wasn’t meant to last between them. Travis, who has a child with Kylie Jenner, and Rihanna moved on from their brief fling, leaving fans speculating about what could have been.
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Hassan Jameel
So, here’s the scoop: Rihanna had a three-year romance with Hassan before they decided to part ways in January 2020. They were pretty low-key about their relationship, rarely stepping into the spotlight together.
Despite keeping things private, Rihanna dropped a bombshell in October 2019 when she confirmed she was head over heels for him. In an interview with Vogue, she spilled the beans, saying:
“Yep, I’m dating. Been in an exclusive thing for a while now, and it’s going great. So yeah, I’m pretty happy.”
But alas, despite the love declarations, the relationship eventually hit the rocks, leaving fans surprised by the sudden split.