Rihanna’s Dating History – A Complete List of Boyfriends

Since her rise to fame, we’ve seen Rihanna find love in a hopeless place with Chris 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 her Fenty Beauty line and Savage x Fenty fashion business. We’ve done so much digging to find out more about her ex-boyfriends and private life!

To see who has been romantically linked to the pop princess, continue reading Rihanna’s dating history below…

Rumored Ex: Shia LaBeouf

Who is He? Actor
Dated In: 2007

According to reports, Shia and RiRi were spotted on a date in Beverly Hills in 2007. The actor confirmed during an interview with Playboy however, that there was no spark between the two.

“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 in an abusive and dramatic ending in 2009. The young star 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 involving a romantic engagement with Beyonce’s husband and rap legend Jay-Z. In fact, many claimed that her record deal with Jay was made in exchange for a quick hook-up.

Although Jay’s infidelity has been made public in recent years, we aren’t convinced with this one! RiRi seems too respectful to get involved in someone else’s marriage – especially Queen Bey’s!

Ex: Drake

Who is He? Rapper
Dated In: 2009 & 2016

This popular pair had romantic rumors circling them 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 RiRi “used him”, Drizzy 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 pop princess 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 certainly difficult to believe her.

It appears the dust has settled on this love story, but we still have hope that something might spark again in the future…

Rumored Ex: Justin Timberlake

Who is He? Singer & actor
Dated In: 2009

Another artist added to Rihanna’s dating timeline is none other than Timberlake. After the release of their song Rehab in 2009, it was reported that Justin and Rihanna were dating. But we aren’t too sure if we believe this one, as Justin was dating his current wife, Jessica at the time. We are putting this one down to good, old Hollywood gossip.

Rumored Ex: Rashard Lewis

Who is He? Basketball player
Dated In: 2009

2009 saw a new route in RiRi’s dating plan with a newfound interest in athletes. This was kicked off with her romantic interest in basketball player Rashard Lewis. The ANTI 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

It seemed like RiRi found a serious connection with Baseball player Matt Kemp in 2009. She even confirmed their relationship during an interview with ELLE, admitting that she felt comfortable, sane and happy with her new beau.

“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 with Matt. 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 apparent.

Dudley confessed in a 2011 interview with Vogue that although he didn’t want the shooting for the video to come to an 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, news was spreading that the actor and singer were secretly dating. Sources told the Daily Mail that Rihanna and Ryan had been hooking up for a few months, but showed no public interest in each other.

This so-called fling was immediately put in the past 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 mega actor, Ashton Kutcher, when pictures of the singer leaving his bachelor pad in the middle of the night leaked. But when RiRi was asked about her romantic involvement with the actor, she appeared uninterested and confirmed that she was, in fact, single!

Rumored Ex: J.R. Smith

Who is He? Basketball player
Dated In: 2012

This duo seemed to instantly hit it off 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. When it was apparent that J.R. Smith was struggling professionally, RiRi took to Instagram to mock him by saying “his a** be hungover from clubbing every night during playoffs”.

The basketball legend didn’t live it down as he fired back with his own ridiculing meme. It’s safe to say that these two definitely won’t be rekindling any form of romance!

Rumored Ex: Leonardo DiCaprio

Who is He? Actor
Dated In: 2015

When the pair 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.

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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”.

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.

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: ASAP Rocky

Who is He? Rapper
Dated In: 2020 – Now

ASAP Rocky has gone from dating Kendall Jenner to being Rihanna’s new boyfriend! These two have been friends for a while now, more specifically since 2013 when he joined her on her Diamonds World Tour and featured on her track Cockiness.

Sparks flew after Rihanna had ASAP feature in her Fenty Beauty campaign and during their dinner in New York (as reported by Page Six). Here’s to hoping this is the real deal! Rih and ASAP look super-cute together!

Rihanna’s dating history has clearly been full of hook-ups and heartache. We’re waiting for the day she properly settles down with her prince charming – hopefully ASAP Rocky is the one.

Who do you think is meant to be with Rihanna? Should it be ASAP or one of her ex-boyfriends? Let us know by commenting in the section below…

Check out our list of facts about Rihanna or scroll through RiRi’s most controversial moments!