They were never in a full-blown relationship, but LaBeouf revealed to Playboy in 2009 that he did go on a date with Rihanna back in ’07. However, it never went past that.
“It never got beyond one date,” LeBeouf said. “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”
2008-2009: Chris Brown
While Chris and Rihanna have known each other since 2005 as friends, they didn’t admit to being in a relationship until around 2008.
By now, we all know their young love was brought to a screeching halt in 2009 after an argument between the couple escalated to Brown getting violent with Rihanna, leaving her with physical injuries.
Since 2009, the two singers have interacted on and off and even shocked the world when they collaborated on two tracks in 2012 (“Nobody's Business,” “Birthday Cake (Remix)”), but they never made the move to get back together permanently.
Rihanna and Chris Brown's 'Nobodies Business': What Do You Think?
Rumors about Rihanna and Drake dating have swirled for years thanks to multiple collaborations between the two artists and their insane chemistry.
During an interview with then-Hot 97 host Angie Martinez, Rihanna reportedly opened up about her and Drake trying it out romantically, but the timing just wasn’t right.
“I definitely was attracted to Drake, but I think it is what it is, like it was what it was,” Rihanna told Martinez. “We didn’t want to take it any further. It was at a really fragile time in my life, so I just didn’t want to get too serious with anything or anyone at that time.”
Drake also opened up about the brief relationship, telling The New York Times he was a "pawn."
“She was doing exactly what I’ve done to so many women throughout my life," he said, "which is show them quality time, then disappear. I was like, wow, this feels terrible.”
It's been a few years -- maybe there's still time for Rihanna and Drake to rih-kindle their romance in the future.
Drake Changes 'Madonna' Lyrics to Rihanna at Jungle Tour Opener in Houston: Live Review
2010: Matt Kemp
Rihanna and professional baseball star Matt Kemp called it quits after almost a year, but this was one of Rihanna’s most public relationships. The couple didn’t shy away from attending events together and showing off PDA. Rihanna even opened up about the relationship during interviews.
“I have a boyfriend. I’m so happy. I feel really comfortable, and it’s so easy,” Rihanna told Elle magazine in 2010.
Chris Brown Says if Rihanna & Leonardo DiCaprio Rumors Are True, 'I Just Tip My Hat'
2015: Leonardo DiCaprio
Rumors swirled earlier this year when the two were reportedly seen engaging in PDA at Rihanna’s 27th birthday party and at a Playboy mansion party. Despite the lengthy flirtation, neither confirmed they were dating at any point.
Rihanna & Travis Scott Put on PDA at NYFW, Justin Timberlake Looks Weirded Out
2015: Travi$ Scott
Rihanna and rapper Travi$ Scott have reportedly been having quite the time during this year's New York Fashion Week. The two have been spotted hugging on each other during the week, but they could just be pal-ing around since they recently debuted a sexy joint ad campaign for Puma.
Only time will tell if Rihanna keeps Travi$ around or gives him the Matt Barnes treatment.
As far as what Rihanna is saying about her current relationship status? She took to her Instagram to put rumors to rest earlier this week (Sept. 14) in true badgalriri fashion: