A Look At Rihanna's Relationship History

When Rihanna first graced the music world with her unique brand of R&B-infused pop and electronica in the mid-2000s, the public was immediately smitten with this enigmatic songstress. And, before long, a whole generation of RiRi stans were born. A nine-time Grammy Award-winner, the multitalented musician has had to work extremely hard to snag the enviable superstar status that she now enjoys. Subsequently, her commitment to her craft has often meant that work comes before play, and Ri has never been one to give up her professional duties for a man.

”Guys need attention,” RiRi once told The New York Times. ”They need that nourishment, that little stroke of the ego that gets them by every now and then. I'll give it to my family, I'll give it to my work — but I will not give it to a man right now.” Accordingly, the singer has generally favored brief dalliances to long-term serious relationships throughout the years, though it appears that she has finally found a lover worthy of that almighty, aforementioned ego stroke.

It takes a lucky man to be in the presence of Queen Ri, and the guys on this list are among a select few who have allegedly locked lips with the Barbadian beauty. Let's take a look at Rihanna's relationship history: keep reading to find out who made her feel like the Only Girl in the world and who was a straight-up Rude Boy (we're looking at you, Drizzy).

Rihanna's first boyfriend, Negus Sealy, dished on their relationship to the Daily Mail. According to Sealy, he first met the singing sensation through "a mutual friend" when she was a mere 15-years-old. The 2011 interview has Sealy's age down as 27, meaning that he was 19 when he first locked lips with Ri. 

"We shared the same sense of humor; she likes to laugh. I guess we pretty much took to each other's character and it was just cool ever since then," Sealy said of his romance with Rihanna. Sealy, who also goes by the nickname Love God, said that his ex is simply too busy to be tied down to one man. "She would be the perfect girlfriend and of course I fancy her — what guy wouldn't?" he confessed. "She's absolutely amazing and gorgeous and she has a very, very strong persona. I am so lucky to have spent so much time with her ... But right now she doesn't have time for anything serious with any guy."

Radar reported that the former teen lovers had rekindled their romance in 2011, noting that Rihanna engaged in some highly NSFW "dirty dancing" with her ex while on holiday in Barbados. However, Rihanna biographer Sarah Oliver has put these rumors to bed (no pun intended), emphasizing that the pair are merely good friends. Whether that means Sealy didn't quite live up to his Love God persona or not, things are strictly platonic between these two.

Remember Josh Hartnett? Everyone's favorite early 2000s pretty boy was reportedly getting super cozy with RiRi circa 2007. At the time, Rihanna gushed about having her heart set on Hartnett. During an appearance at the World Music Awards (via Mirror), Rihanna apparently said of Josh, "I've fallen for him big time. I would be lying if I told you we were not more than just friends. He is so hot and he is really sweet to me. When we hang out it feels right — even though it's still pretty new."

However, she later emphatically said that the pair were not dating. "I went to [the New York club] Pink Elephant, and he came by," she told Allure (via People). "All of a sudden, the next day, I'm seeing that we were kissing and hugging up each other." She continued, "You can't even go out with a friend who's a celebrity and have a good time without people making [bleep] up. Well, at least he's good-looking, right?" That he is indeed, Ri.

A couple of years later, she was also linked to Shia LaBeouf, who dished on their one and only date to Playboy (via MTV). The actor claimed that he didn't pursue a relationship with Ri beyond the first date because "The spark wasn't there. We weren't passionate about each other in that way." Considering LaBeouf's shocking behavior in recent years, we can't help but think this was for the best.

According to Hollywood Life, Rihanna and Chris Brown first met as teens with dreams of fame and fortune. They began dating and went public with their romance in 2008, per CNN. 

But things took a devastating turn when it was revealed that Brown had viciously beaten Rihanna. According to The Guardian, Rihanna and Brown were supposed to perform at the Grammy Awards in 2009, but they mysteriously pulled out. It soon became quite apparent why. TMZ obtained an official police report, which detailed the extent of Brown's brutal assault on his then girlfriend, and published photos of the singer's horrific injuries. Brown agreed to a plea deal for the charge of felony assault and was given 5 years probation, per TMZ.

A year after the traumatic ordeal, Rihanna reflected on surviving the abuse in an interview with Marie Claire. "Eventually, I remember waking up one day and I knew I was over it," she said while apparently in the midst of tears. She continued, "I was very lost. I have to say I felt really confused. I hate talking about it but it was really crazy because I felt so out of touch with myself ... It's scary because nothing you say or do feels like it's you." The confusion that Rihanna felt is typical of many survivors of domestic violence, as highlighted by The Mend Project. In opening up about her experience, Rihanna helped to amplify the voices of domestic abuse survivors.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Drake has made no secret of his infatuation with Rihanna. The pair were linked in May 2009 when Page Six reported that they were hanging at Lucky Strike where Ri was "drinking whiskey and apple juice and making out with him all night." However, they first met years earlier, when Rihanna was filming the music video for "Pon de Replay" in Toronto, as Drake revealed at the VMAs.

The couple had frequent ups and downs, with Drake often complaining about his ex to the press. In 2010, he claimed to The New York Times that Rihanna used him like "a pawn," then, a year later, he told Elle that RiRi "hurt" him. But it was clear that Drizzy was dizzy in love.

At the 2016 VMAs, Drake gushed about Rihanna when presenting her with the Vanguard Award. "She's someone I've been in love with since I was 22 years old," he confessed as Rihanna rolled her eyes, not looking entirely enthusiastic with this bold declaration of love in front of a live audience. Sure enough, Rihanna admitted in a Vogue interview that Drake's speech made her feel uneasy. "Waiting through that speech was probably the most uncomfortable part. I don't like too many compliments; I don't like to be put on blast," she said. When asked whether she was still close with Drizzy, she revealed that they "don't have a friendship now, but we're not enemies either."

After her traumatic relationship with Chris Brown, Rihanna reportedly found comfort in a new man, basketballer Rashard Lewis. The singer was spotted gazing courtside at Lewis during a game in 2009. "Rihanna is trying to get to know Rashard," an insider told Daily News. "She's digging on him, and she hopes the feeling is mutual." Alas, nothing seemed to materialize beyond this gossip.

Around this time, she was also linked to Justin Timberlake. Outlets reported that he was "cheating with Rihanna" on Jessica Biel after rumors surfaced of RiRi apparently giving JT a private lap dance at a club. "He is really into her," a source told Hollyscoop (via Marie Claire). "Justin and Rihanna have been seeing each other for the past few weeks." 

The following year, rumors persisted, with Rihanna's pal telling Daily Star (via Digital Spy) that "She's getting close to Justin again and it's getting hot." The insider claimed that things were super steamy between the purportedly lusty pair. "Rihanna called a friend and said she had a sexy little secret to share," the source alleged. "She started laughing and said, 'Don't trip, but I have hooked up with Justin.' She said it was really good, hot and wild and that they have some of the best make-out sessions she's ever experienced." But considering that the duo have worked together, it seems unlikely that these sightings were anything other than friendly outings between musically blessed pals.

During an Instagram Live (obtained by Hollywood Life), mid-2000s hip-hop one hit wonder Soulja Boy cranked out some absurd claims. In 2017, the rapper told his millions of Insta followers that he was responsible for the rift between Chris Brown and Rihanna, with whom he claimed he had a tryst "four or five" years earlier. "What happened?" he asked. "Me and Rihanna was in the hotel room, Chris [Brown] called my phone, asking if I was with Rihanna [and having sex]." Then, apparently addressing Brown, Soulja Boy said, "Nobody would have known... if it wasn't for you. You're an idiot. You exposed yourself. Now everybody knows I had both of your b****es."

Soulja Boy appeared on "Hollywood Unlocked" to further address his supposed relationship with the "Diamonds" star, claiming that she was the one who initiated their fling. "She called my management ... I've never had nothing my whole life — that's Rihanna!" The rapper then alleged that Rihanna called him and invited him back to her hotel room at 1am, dressed in a skimpy robe, before confiding in the rapper about Chris Brown's violent treatment of her. "What he really mad about is that I was with Rihanna," he said of his beef with Chris Brown, alleging that an irate Brown called him to ask whether he had sex with his ex.

It should be noted that Rihanna hasn't confirmed any of Soulja Boy's assertions, so perhaps he should crank that gossip.

Rihanna and baseball star Matt Kemp dated for around a year and appeared to be quite the lovestruck power couple. They first met through mutual friends in late 2009 and it didn't take long for the pair to hit it off, per People. Subsequently, Just Jared published snaps of the hot and heavy couple smooching before Kemp caught a flight to Arizona.

In 2010, RiRi gushed about the exciting new relationship in an interview with Elle. "I have a boyfriend. I'm so happy," she enthused. "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." Kemp was equally smitten, telling Us Weekly (via Cosmopolitan), "Yeah, that's my girl! She's just a fun person. I love to be around her. She's a great person in my life and I'm happy I'm with her."

Sadly, despite their mutual fervor, the couple called it quits at the end of 2010. An insider told Us Weekly that Rihanna "basically was just over it." They added that Kemp struggled to keep up with the singing superstar's hectic lifestyle. "He just can't keep up with her crazy travel schedule. Matt's sick of always following after her like a puppy dog all over the world. He wants something more normal," the source alleged.

In 2011, Rihanna was apparently feeling hot and bothered over boxer and model Dudley O'Shaughnessy. During her time in the U.K., the Daily Mail reported that Ri was partying with the brooding Brit well into the early hours of the morning and the two left together in a limo. She had previously set sights on the hunk when filming her music video for "We Found Love," which stars O'Shaughnessy and sees the pair engaging in a series of passionate make-out sessions before things take a darker turn. The duo got into trouble when making the vid, which was filmed on a farm in the U.K., when local farmer Alan Graham asked the songstress to "cover up," per the BBC.

But, according to insiders, Rihanna could hardly cover up her lust for her co-star. "Rihanna was making no secret that she fancied the pants off Dudley," an insider told The Sun (via Daily Mail). "They hit it off straight away. She had seen his modelling shots and other pictures when he was a boxer. Rihanna took every opportunity to get close to him and at one point she was sitting in his lap during a break from filming."

However, it seems that Rihanna's supposed ardor didn't manifest into a relationship. During an appearance on "The Ellen Show" at the time, the host showcased a photo of O'Shaughnessy and his steely peepers, but Ri firmly insisted that she was "not dating anybody."

Ashton Kutcher has certainly attracted some of the entertainment industry's finest. Before he tied the knot with Mila Kunis – and after he called it quits with Demi Moore — he was linked to Rihanna. In 2012, Radar reported that Rihanna was seen leaving the newly-separated Kutcher's home in the early hours of the morning after a four hour visit. 

The Sun (via Daily Mail) then claimed that the pair had been enjoying an "eight-week fling," adding, "The flirting began as soon as Rihanna and Ashton met and swapped numbers," a source alleged. "That moved onto texts and arranging to meet. They snuck off to a Santa Monica hotel a few weeks ago. They are two single people having a fling, so thought it would be best to meet in secret." The insider went on to purport that RiRi was studying Kabbalah for Kutcher. "If she and Ashton are getting really close, she wants to be able to understand it," they claimed.

During a press conference for "Battleship," Rihanna was asked to address the rumors. "Things are clearly going brilliantly in your career. I just wondered if you are as happy in your private life, and will we see a certain Mr. Ashton Kutcher perhaps making a trip over here?" a reporter asked, prompting some major side-eye from Ri. "Wow, how disappointing was that question?" Rihanna lamented, adding, "I'm happy and I'm single, if that's what you're really asking?"

Karim Benzema is a French international soccer star, who plays for Real Madrid. The sportsman was linked to Rihanna in 2015, though their apparent romance seemed to fizzle after less than two years. In June 2015, E! reported that the pair were enjoying a summer of love. After being snapped snuggling at a restaurant, an onlooker dished on their dalliance. "Rihanna and Karim were seating across from each other," the source revealed. "There were about four people at the table and a few more in another table from the same party. They came separately and they were speaking French at some point." We can't help but wonder if Ri and Benzema were sharing more than French tongues.

The following month, E! reported that "the two have a great time together and are taking things slow. They have an amazing connection and always have a wonderful time when they are together."

In 2017, those close to Benzema said the couple had called it quits. Sources told Spanish mag Don Balon Rosa (via The Sun) that it was Ri who called off the relationship, apparently telling her beau that she simply wasn't over her ex, Chris Brown. "Rihanna loved Karim, and with him she had a lot of fun," the insider said. "But she told him she did not want to break his heart, and she confessed that she'll always love Chris Brown. Rihanna said it was difficult to compete."

Formula One champ Lewis Hamilton was spotted getting close to Rihanna after snaps surfaced of the pair vacationing in Barbados, per Page Six. The attractive duo soaked up the sun in skimpy swimwear during their trip in August 2015. There was a touch of overlap between her romance with Karim Benzema and alleged dalliance with Hamilton. "Rihanna is dating now and she hasn't put a label on anyone," a source told E!. "She is still talking to Karim but she is also talking to Lewis and keeping her options open. She is not at any point in her life now ready to settle just for anyone but she is enjoying the time she has with her friends and also focusing on work."

Accordingly, Page Six reported that the two appeared rather intimate at a nightclub, with a source telling the outlet, "They definitely looked cozy. She was dancing next to him, and he poured most of her drinks." When E! asked the champ about the status of his relationship with Ri, he said, "I've known Ri for a long time. We've been friends for a while. We get to hang out every now and again."

The alleged romance appeared to wane some time after. In 2018, Hamilton admitted to The Times, "When you travel as much as I do it's hard to keep up a relationship." Subsequently, we can't blame the pair for not pursuing a romance when it's all work, work, work.

He may be embroiled in the antics of the Kar-Jenners — and the aftermath of his disastrous Astroworld festival – these days, but Travis Scott enjoyed a low key romance with Rihanna during a seemingly more simple time.

In September 2015, E! announced that Rihanna and Scott were "officially dating." A source claimed, "It's already very serious. He's very into her." TMZ published snaps of the rumored couple in the throes of a steamy make-out sesh at a fashion week afterparty. It seems that Rihanna's eagerness to pack on the PDA with Scott may be due to his, ahem, skills in the sack. "Rihanna and Travis are uncontrollable when it comes to sex," a source alleged to Hollywood Life.

In an interview with Complex, Scott remained coy when asked about RiRi, but he did describe his reported lady love as "creative," "inspiring," and a "muse." The outlet also notes that Scott was tardy "because he's holed up with Rihanna, his recently rumored love interest/girlfriend/friend-with-benefit."

Complex editor Lawrence Schlossman later said that Scott was infuriated with him for revealing his romance with Rihanna. "I broke the news about him and Rihanna, which they told me not to do," Schlossman told the "Throwing Fits" podcast. Why? Well, apparently Ri was embarrassed for the public to know she was dating Scott, hence their lowkey romance. "Rihanna's like, 'Don't tell anyone that I'm smashing Travis Scott, please. [It's] obviously embarrassing as f***,'" Schlossman added.

Hassan Jameel is a Saudi businessman with a whopping net worth of almost $2 billion thanks to being a member of the 12th richest Arab family in the world, per Forbes. He was first linked to Rihanna in 2017 after People reported that the two were spotted smooching during a coffee date. The attractive couple then celebrated spooky season together, with RiRi dressed as Kylo Ren and Jameel as a penguin. "Rihanna and Hassan were canoodling all night," an onlooker told People regarding the loved up couple.

One of Rihanna's most serious relationships, she and the wealthy businessman were going strong for years. Speaking with Sarah Paulson for Interview Magazine in 2019, Rihanna said the romance changed her life for the better. Notably, she had finally been able to make time for herself. "I got into a new relationship, and it matters to me. It was like, 'I need to make time for this,'" she explained. "Just like I nurture my businesses, I need to nurture this as well ... On my calendar we now have the infamous 'P,' which means personal days." When Paulson asked Ri about the seriousness of the entanglement, the songstress said "Of course I am" in love with Jameel.

Sadly, Us Weekly reported that the couple had parted ways in January 2020, after a grand total of nearly 3 years. Sources told People that "Their lives were too different and it was hard to maintain a relationship."

Talk about musical power couples. Rihanna and A$AP Rocky were initially spotted getting close at a concert in New York in 2020, though they first collaborated almost a decade earlier on the remix for the saucy track "Cockiness (Love It)." Shortly after her split with Hassan Jameel in January 2020, a source dished to The Sun about Rihanna's new liaison. "They shared a hotel suite during that trip in New York," the insider revealed. "However, Rihanna is reluctant to put a label on it as it's so soon after Hassan. They're really enjoying each other's company and taking things easy as it's still early days."

By December 2020, People reported that Rihanna was "very happy" with Rocky and the pair had "been inseparable." In an interview with GQ, Rocky declared his love for Ri. "The love of my life," he revealed, adding, "I think when you know, you know. She's the One."

In January 2022, Rihanna and Rocky revealed that they were expecting their first child after the stylish duo were snapped cradling Ri's baby bump. "Being with Rocky opened her up to the idea. She couldn't be happier and is so excited to be a mom," a source told People. The announcement appeared to spark jealousy in Rihanna's ex, Drake, who swiftly posted a series of cryptic, morose posts on Instagram. It seems that some people just had to rain on Ri's parade. Sorry Drake, you'll never be under her umbrella.