Since her rise to fame, we’ve seen Rihanna find love in a hopeless place with Chris Brown and work, work, work on her fling with Drake.
Most of RiRi’s love life however, has been kept under wraps, with media attention focusing on her success with Fenty Beauty and her Savage X Fenty fashion empire. But let’s be real, the Navy has always been curious about the men Rihanna has dated. From her headline-making romances and rumored flings to the A-list men she’s been linked to over the years, there’s plenty to unpack about the superstar’s relationship history.
So, who has Rihanna dated, and who has she been romantically linked to? From her highly publicized relationship with Chris Brown to her love story with longtime partner A$AP Rocky, we’re breaking down Rihanna’s dating history, rumored ex-boyfriends, and everything we know about her journey to finding love. Want to enter your favorite pop girlie’s romantic lore? Keep scrolling!
FYI: Other than her official romances, this list also contains guys that Rihanna was *rumored* to be dating.
Who is Rihanna Dating Now?
Rihanna is currently in a relationship with rapper A$AP Rocky. The couple, who have been friends since 2013, share three children together. More on that below!
Rihanna’s List of Boyfriends Over the Years
Jump to:
- Shia LaBeouf
- Chris Brown
- Jay-Z
- Drake
- Justin Timberlake
- Rashard Lewis
- Matt Kemp
- Dudley O’Shaughnessy
- Ryan Phillippe
- Ashton Kutcher
- J.R. Smith
- Leonardo DiCaprio
- Travis Scott
- Hassan Jameel
- A$AP Rocky
Rumored Ex: Shia LaBeouf
Who is He? Actor
Dated In: 2007
According to reports, Shia and Rihanna were spotted hanging out in 2007. The actor confirmed during a 2009 interview with Playboy however, that there was no spark between the two [via E Online].
“It never got beyond one date,” he said. “The spark wasn’t there. We weren’t passionate about each other in that way…” The feeling was mutual and the pair remained in contact as friends only.
Ex: Chris Brown
Who is He? Singer
Dated In: 2007-2009 & 2012-2013
What started off as a fairytale relationship in 2007 ended up with an abusive and dramatic ending in 2009. Rihanna was lucky enough to find — what seemed like — the perfect match in fellow singer, Chris Brown.
In 2007, the pair met and embarked on a low-key relationship, but it made public news in 2008, hogging headlines for months after.
After a heated disagreement in 2009, images of a beaten Rihanna broke the Internet and put an immediate end to their dreamy relationship. In what was one of Chris Brown’s biggest scandals, he was ordered to five years of probation and was required to stay at least 50 yards away from RiRi.
Surprisingly though, after a few years of restraining orders and heartache, the controversial celebrities rekindled their romance and sparked an old flame. Although Rihanna admitted that she’d “forgiven” Chris and that he was the “love of her [my] life”, it sadly didn’t last long as they decided to split for good in March 2013.
Rumored Ex: Jay-Z
Who is He? Rapper
Dated In: 2009
The Barbadian singer has also been the subject of rumors linking her romantically to Beyoncé’s husband and rap mogul Jay-Z. However, the speculation took a different turn when an old clip resurfaced in 2024, showing Rihanna recalling her first meeting with Jay-Z in 2005, when she was just 16 and auditioning for his Def Jam record label.
Jay-Z reportedly joked that she could either leave through the door with a signed record deal or through a window on the 29th floor. The clip reignited conversations about their early relationship, but there is no confirmed evidence that the two were ever romantically involved.
Rumored Ex: Drake
Who is He? Rapper
Dated In: 2009 & 2016
Romance rumors were circulating this popular couple for years, and although Drizzy’s admiration of RiRi was evident, we never really saw a mutual return. From Drake’s feud with Breezy over her, to admitting that she “used him,” Drake has taken many Ls throughout his relationship with Rihanna.
This was unmistaken after his very public (and cringe-worthy) confession of how much he loves RiRi at the 2016 VMAs when the star swerved his kiss on stage — for all to see!
Rihanna has denied ever being with Drake, but after being spotted holding hands, collaborating on several tracks, and getting steamy in their Work video, it’s difficult to believe her.
Rumored Ex: Justin Timberlake
Who is He? Singer & actor
Dated In: 2009
Another name that pops up in Rihanna’s dating history is none other than Mr. Timberlake himself! Following the release of their song Rehab in 2008, rumors began circulating that Justin Timberlake and Rihanna were secretly dating. But this one deserves a major side-eye, considering Justin was already dating his now-wife, Jessica Biel, at the time.
Reportedly, Rihanna even reassured Jessica that nothing was going on between them. So, was there really something brewing behind the scenes, or was this just another case of Hollywood gossip doing what it does best? Without any solid confirmation, we’re filing this one under rumored romance.
Rumored Ex: Rashard Lewis
Who is He? Basketball player
Dated In: 2009
2009 saw a new route in RiRi’s dating game with a newfound interest in athletes. This was kicked off with her romantic interest in basketball player Rashard Lewis. The best-selling singer was pictured leaving Rashard’s apartment building, but nothing further seemed to come from it.
Ex: Matt Kemp
Who is He? Baseball player
Dated In: 2009 – 2010
Rihanna seemed to find a serious connection with baseball player, Matt Kemp in 2009. She even confirmed the relationship during an interview with ELLE, admitting:
“I have a boyfriend. I’m so happy. I feel really comfortable, and it’s so easy. I have such a chaotic life, but at the end of the day, that is just my peace. It keeps me sane, really, talking to him and talking to my family.”
But as the year came to an end, so did her relationship. Always the hopeless romantic, it was rumored that RiRi went back for reconciliation in 2013, but nothing was ever officially confirmed.
Rumored Ex: Dudley O’Shaughnessy
Who is He? Actor & model
Dated In: 2011
Rihanna’s on-screen love interest in her We Found Love video was rumored to be an off-screen affair, too. Although nothing was confirmed or denied, the pair’s chemistry in Rihanna’s video was as clear as day.
Dudley confessed in a 2011 interview with Vogue that although he didn’t want the shooting for the video to end and enjoyed being in RiRi’s presence, they were “just mates.”
Rumored Ex: Ryan Phillippe
Who is He? Actor
Dated In: 2011
Back in 2011, rumor had it that Rihanna and Ryan Phillippe were secretly dating. Sources told the Daily Mail that they had been hooking up for a few months, but showed no public interest in each other.
This so-called fling was immediately put to bed however, when onlookers later claimed that the Cruel Intentions actor was rejected when he approached RiRi at a pre-Grammy event that year.
Rumored Ex: Ashton Kutcher
Who is He? Actor
Dated In: 2012
It was also reported that RiRi enjoyed an eight-week fling with Hollywood heartthrob Ashton Kutcher after photos emerged of the singer leaving his bachelor pad in the early hours of the morning.
But when Rihanna was asked about the alleged romance at a press conference for her movie Battleship in March 2012, she wasn’t exactly impressed. Calling the question “disappointing,” RiRi insisted, “I’m happy and I’m single, if that’s what you’re really asking.”
Rumored Ex: J.R. Smith
Who is He? Basketball player
Dated In: 2012
This duo seemed to hit it off instantly in 2012 with claims that they were extremely flirtatious in a New York nightclub and showing some serious PDA. However, the relationship turned sour later that year. It was rumored that J.R. Smith was struggling professionally, and so RiRi took to Instagram to mock him by saying “his a** be hungover from clubbing every night during playoffs.”
The former basketball player didn’t live it down as he fired back with his own ridiculing meme. Safe to say these two definitely won’t be friends for a while.
Rumored Ex: Leonardo DiCaprio
Who is He? Actor
Dated In: 2015
When Rihanna and Leo were spotted getting cozy in a Paris nightclub in 2015, it was only expected that dating rumors would fly. Sources claimed that Leo and Rihanna even locked lips and ended up at the same after-party together.
With fans dubbing the couple ‘Lihanna’ and ‘Rihcaprio, this sounded like a Hollywood match made in heaven, but nothing was ever confirmed from either party. When asked about the hook-up by Hello!, Rihanna just insisted that she was “single.” The pair were later seen at Coachella together in 2016, but nothing came from it.
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Rumored Ex: Travis Scott
Who is He? Rapper
Dated In: 2015
Way before his Kylie Jenner days, Travis was reportedly linked to the gorgeous RiRi. These rumors came after a joint marketing collaboration with Puma and their evident closeness during NY Fashion Week.
Insiders even claimed that Rihanna had fallen hard for the Astroworld creator, whom she had apparently been with for a year. But just a short week later, Travis was spotted hanging out with the Kardashian clan, putting a clear end to his budding romance with Rihanna.
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Ex: Hassan Jameel
Who is He? Toyota Heir
Dated In: 2017 – 2020
In 2017, Rihanna quit dating celebs and found a new love interest in Saudi billionaire, Hassan Jameel. Although they didn’t publicly confirm their relationship, the pair were spotted at numerous events together and on secret dates, with RiRi even giving a shoutout to his new investment Riviano Motors.
During a 2018 interview with Vogue, RiRi hinted at the relationship by saying, “I used to feel guilty about taking personal time, but I also think I never met someone who was worth it before,” making us think that Hassan was the exception.
While the low-key pair never confirmed any serious relationship, we did suspect that RiRi was in this one for the long haul — until their breakup in 2020 after three whopping years. According to People, “Their lives were too different and it was hard to maintain a relationship.”
Boyfriend: A$AP Rocky
Who is He? Rapper
Dated In: 2020 – Now
A$AP Rocky has gone from dating Kendall Jenner to becoming Rihanna’s longtime partner and the father of her three children. Talk about a plot twist I can get behind!
The pair have known each other for years, first collaborating on Rihanna’s 2012 remix of Cockiness (Love It) before Rocky joined her Diamonds World Tour in 2013. Although dating rumors swirled for years, their friendship eventually turned romantic in late 2019. By November 2020, the two were spotted enjoying a dinner date in New York City.
In 2021, Rocky publicly called Rihanna “the one,” and the couple soon began building a family together. Their first son, RZA, arrived in May 2022, followed by their second son, Riot, in August 2023. Then, in September 2025, they welcomed their third child, a daughter named Rocki Irish Mayers. From Rihanna’s iconic pregnancy reveals to their loved-up red-carpet appearances, these two have given us plenty of adorable moments over the years.
While fans have long speculated that the couple have secretly tied the knot, Rocky has kept everyone guessing. When asked about the rumors in 2025, he cheekily responded, “How you know I’m not already a husband?” before adding that he still wasn’t going to confirm it. So, as of right now (October 2026), their marital status remains publicly unconfirmed.
One thing’s for sure: Rih and Rocky have built a whole little family together, and I’m forever obsessed!
This post was originally published in 2021, but was updated in 2026 to include more recent details on Rihanna’s relationships.
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I think she needs to lay the ghost of her drunken/abusive father to rest before she will ever find happiness with a man. Many of her beaux so far are not enouraging in that respect.
I think me.