She Found Love! Rihanna's Dating History

Since she first sang her way into our hearts in the mid-2000s with hits like “Umbrella,” “who is Rihanna dating” has been asked as much as “what is her latest hit song?” Many know all about her tumultuous relationship with Chris Brown, but did you know that she also had a date with Shia LaBeouf?  

MORE: Rihanna has become friends with Princess Meghan Markle!

From the rumored relationships — such as Ashton Kutcher and Justin Timberlake — to her confirmed and longtime (i.e. serious) boyfriends like baseball player Matt Kemp, it is all revealed in this Rihanna relationship history chronicle.

MORE: Rihanna's best Fenty lingerie pics!

One thing is clear, Rihanna does not have a type. From sports stars, film stars and singers, she is an equal opportunity dater!

How Hassan Jameel, the Saudi billionaire, and Rihanna met is not quite clear, but on June 27, 2017, they were seen together in Ibiza, according to Vogue. They have enjoyed the other’s company ever since. There are rumors that the pair first hooked up in Tokyo (where Jameel went to college) back in April of 2017. Jameel, worth approximately $1.5 billion, and the “S.O.S.” singer have not hidden their relationship after the “getting to know you” stage. The automobile entrepreneur is no stranger to dating famous women — he and Naomi Campbell were seen together for a period. It seemed to get serious when they spent that birthday at the Staples Center at a Los Angeles Lakers game — not exactly a hub of privacy!  

Early in 2016, RiRi and Oscar winner Leonardo DiCaprio were seen together for a spell. Their relationship was totally casual, according to Elle, whenever they shared an area code. Since then, the pair was spotted across the globe simply hanging out. It is possible that the movie star and the singer are now merely just friends. That would fit his pattern, given that DiCaprio has a thing for models (as his dating history has shown), and they’re usually under the age of 25. Rihanna is neither. This could explain why whatever she and the Once Upon a Time in Hollywood star had was never fully pursued. In February of 2018 when she celebrated turning 30 with a bash, Vanity Fair reported that DiCaprio snuck in to her utter delight.

Rihanna and the Canadian rapper were connected beginning in 2005, according to Billboard, when Drake met her on the Toronto set of her “Pon De Replay” video. According to the music mag, their first date wasn’t actually until May of 2009. Timing is everything. She had just split from Brown, and things with Drake never fully materialized. She saw him as more of a friend, but he saw things differently. They teamed up for 2010’s “What’s My Name,” igniting rumors the pair were an item (again). In 2014, The Mirror reported the couple were in London holding hands, but Rihanna told Vanity Fair that the duo were “not dating.” In 2016, Drake professed his love for her as he introduced her at the MTV VMAs for her Vanguard Award. After the awards show, they were spotted out on the town, according to Billboard. It appeared to go nowhere, and they called it off when it became clear that they were better friends than anything more. Sadly, in a new Vogue interview in 2018, she stated, “We don’t have a friendship now, but we’re not enemies either. It is what it is.”

Who would have thought that the Barbados-born chanteuse would have anything in common with Kylie Jenner? They do, and it comes in the form of Jenner’s baby daddy, rapper Travis Scott. Rihanna and Scott hooked up briefly during 2015 after sparking romance rumors with their obvious chemistry during New York Fashion Week, according to E! News. After being seen on four separate evenings during that fabled fashion week, and again during Paris Fashion Week, the pair were never again seen together romantically. It appeared as if those two were one month and done. A source close to the “Shut Up and Drive” singer told E!, “All of her friends think he is gonna be a keeper.” Guess not.

Thankfully for him, the Cleveland Cavaliers player can be known for more than simply being the guy who was not aware of how much time was left on the clock during game one of the NBA Finals in 2018. He hooked up with the “Diamonds” singer at some point during 2012. On the basketball side of things, the player has had an impressive career. Sadly, J.R. Smith will likely be most known for having cost the Cavaliers a chance to win the first game of the NBA Finals against the Golden State Warriors … and hooking up with Rihanna when he was with the New York Knicks during 2012. They were spotted together at nightclubs across New York City and even in Miami, according to Sports Illustrated.

Rihanna and Ashton Kutcher hooked up? You bet! Their eight-week fling, as the Daily Mail called it, began when the pair met at a Hollywood house party in 2012. But Kutcher would eventually start dating Mila Kunis and the stars of That 70s Show would get serious ending anything more with Rihanna.

Surely Ryan Phillippe never had any Cruel Intentions towards Rihanna, it just didn’t work out between the pair after they dated for a few months in early 2011, according to Us Weekly. The “Stay” singer was reportedly the first woman that Phillippe dated after splitting from wife Reese Witherspoon.

Music videos have been known (like film sets) to provide a landscape for people to get together romantically or at least physically. When Rihanna set out to make the video for “We Found Love,” her track with DJ extraordinaire Calvin Harris (an ex of Taylor Swift), she met Dudley O’Shaughnessy (a boxer-turned-model) and the pair didn’t necessarily find love, but they did reportedly hook up for a night or two, then again briefly in 2013.

Former Washington Wizard basketball player Rashard Lewis and Rihanna went on a few dates back in 2009. Again, as a professional athlete, he is constantly traveling and as a singing superstar (and actress), RiRi is hardly in the same place more than a few nights at a time. Schedules keep putting an end to any potential love matches for the “Umbrella” singer. However, the paparazzi did have fun catching Rihanna leaving Lewis’ apartment in nothing but a hoodie after spending the night — as chronicled in Sports Illustrated.

Perhaps Rihanna helped Justin Timberlake bring sexy back? The two were both famous singers and aspiring actors with the Midas touch. Unfortunately, the same couldn’t be said for their love life. Timberlake and Rihanna couldn’t make it work beyond several date nights across Manhattan during 2009 when his relationship with Jessica Biel had hit the skids, according to Ranker. Clearly, the actress and The Social Network star worked it out as they have been married since October 19, 2012.

One date was it, according to Parade. There are a lot of men out there (and women) who would treasure the chance to spend a single evening with Rihanna. “It never got beyond one date,” LaBeouf explained. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.” That’s the haps when it comes to the Transformers star and the Barbados native.

This one is complicated ... Rihanna and R&B superstar Brown dated seriously from 2007 until 2009. It famously ended when the R&B singer was arrested for assaulting her on the night of the Grammys. They left a Grammys party, and he received a text from another woman. The “Don’t Stop the Music” singer didn’t appreciate that, and they fought. “He had no soul in his eyes. Just blank,” she recalled to Diane Sawyer for Good Morning America of the assault (chronicled at CNN Entertainment). "I caught him in a lie, and he wouldn't tell the truth. And I wouldn't drop it." The pair reconciled in 2012, but it was brief. The fierce backlash she received from her fans set her straight, and she walked away from the “Kiss Kiss” singer.

After meeting on the set of MTV’s TRL, Josh Hartnett and Rihanna dated briefly, according to Zimbio. Although at the end of 2007, the “Rude Boy” singer reported that nothing ever happened between the two. She told Allure, “I went to the New York club Pink Elephant, and he came by. All of a sudden, the next day, I’m seeing that we were kissing and hugging up each other. You can't even go out with a friend who's a celebrity and have a good time without people making (expletive) up ... well, at least he's good-looking, right?"

The rumor mill was all sorts of crazy with the idea that Jay-Z and Rihanna’s connection went beyond musical collaboration as they were crafting her Good Girl Gone Bad album. RadarOnline.com Online explored the topic and, of course, both parties denied it ever occurred. To this day, their potential hookup still gets attention. It might stem from their chemistry that was undeniable with “Umbrella.”