8 Famous Men Who've Been Lucky Enough to Score a Date With Rihanna

The Transformers actor was rumoured to be dating Rihanna after they were spotted eating at a restaurant together in Beverly Hills in the Summer of 2007. Nearly two years later, LaBeouf told Playboy that the two did indeed go out on a date during that time but that it just didn’t work out, revealing, “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”

Chris and Rihanna were friends for a few years before they admitted to being in a relationship in 2008. Their relationship came to a shocking halt a year later when Brown physically assaulted her. Still, the two dated on and off for quite some time after and even released two tracks together, “Birthday Cake Remix” and “Nobody’s Business.”

The singer dated the LA Dodgers baseball player for almost a year in 2010. During their time together, Rihanna opened up about their relationship, saying, “I’m so happy. I feel really comfortable, and it’s so easy. [The relationship] is just my peace. It keeps me sane.” Similarly, Kemp gushed, “She’s just a fun person. I love to be around her.” Unfortunately, the duo broke up in December 2010, and four months later, the Barbados beauty opened up about the split in Vogue magazine, saying, “I just let it go. I don’t ever want to have to depend on a relationship. I think it’s a really special thing to find love. It’s beautiful. Nothing can match it, but I want to make sure I find other things in life that I love – besides love.”

The “Work” singer briefly dated the rapper in 2015. After turning up the heat at New York Fashion Week, sources confirmed to E! News that the two were indeed together. While it’s unclear when their romance fizzled out, Scott did serve as the opener for her Anti World Tour in 2016.

Rumours first began swirling that DiCaprio and Rihanna were hooking up after it was reported that the actor helped the star plan her 27th birthday party back in January 2015. Insiders told People that the duo got flirty on the dance floor, and weeks later, Rihanna linked up with DiCaprio at a club in Paris. Although sources claimed the two were “just friends,” in April 2016, the pair were spotted together yet again at the Neon Carnival during Coachella.

Drake and Rihanna were rumoured to have dated on and off from 2009 to 2016. Shortly after the “Umbrella” singer’s split from Chris Brown in 2009, she and Drake were spotted making out at the Lucky Strike bowling alley in LA. While Rihanna has always insisted that they’re just friends, during an appearance on The Ellen DeGeneres Show in 2013, Drake admitted that he did indeed date Rihanna. The two have worked on several duos together, including “What’s My Name?” and their latest, “Too Good.”

In 2016, the couple rekindled their romance, and a source told People that they had been “secretly dating for months.” Drake bought a billboard in LA to offer his congratulations ahead of Rihanna receiving the Michael Jackson Video Vanguard Award at the MTV VMAs, and on VMAs night, he hopped on stage to present Rihanna with her trophy. They even got matching shark tattoos just before splitting again in October 2016. “She doesn’t want to be held down,” a source told Us Weekly. “They will always be close. If they end up together, it could happen, but not now.”

Rihanna kicked those dating rumours into high gear when she was photographed making out with Saudi billionaire Hassan Jameel in Spain in June 2017. The pair dated for three years before calling it quits in January 2020. “Their lives were too different and it was hard to maintain a relationship,” a source told People at the time. Jameel, who was also linked to Rihanna’s former pal, Naomi Campbell, back in 2016, is a Saudi businessman. Rihanna, of course, is a multi-platinum selling artist who additionally runs Fenty Beauty, Fenty Skin, and Savage X Fenty.

Months prior to their breakup, Rihanna opened to Interview about incorporating more work-life balance into her life. “I got into a new relationship, and it matters to me. It was like, ‘I need to make time for this.’ Just like I nurture my businesses, I need to nurture this as well,” she told the outlet. “I’ll shut things down for two days, three days at a time. On my calendar we now have the infamous ‘P,’ which means personal days. This is a new thing.”

The pair is expecting their first child together, but Rihanna and A$AP Rocky have been friends and collaborators for a decade now. I mean, who can forget when the rapper, whose real name is Rakim Mayers, grabbed Rihanna’s butt and kissed her on the cheek during their 2012 MTV Video Music Awards performance? Though the exact timeline of their relationship is murky, ASAP Rocky finally confirmed his romance with Rihanna in May 2021, calling the Fenty Beauty founder “my lady” in a GQ interview. “[Rihanna] amounts to probably, like, a million of the other ones,” he said, adding that she’s “the love of my life.” Aww, congrats to the happy couple!