Rude Boys: The Many Boos, Rumored Side Pieces and Boyfriends of Rihanna

July 27, 2012  |  
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With former boos Chris Brown and Drake exchanging more than words during a bloody brawl at a New York city nightclub recently, past gossip pinning the Bajan singer with Ashton Kutcher, and reports that Rihanna and Chris Brown were seen kissing as they met up during their vacations in Saint-Tropez this week, Rihanna’s love life has been all over the news lately.

With all the public relationships Ri-Ri has had, it would be surprising if there wasn’t any drama or gossip. After all, Rihanna definitely seems to have a thing for famous and fine men. Normal guys just don’t seem to cut it for her!

At age 24, the singer has already had her fair share of high profile flings, rumored boo-ships and relationships. Here are the famous cuties (that we know about) that have been with, dated, or been rumored to have found love in a hopeless place with the superstar over the years.

Shia LaBeouf

This is probably the shortest of Rihanna’s celebrity flings. Shia LaBeouf openly admitted that the two went on a date in the summer of 2007. After one date, LaBeouf claimed, “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.” What was probably the most interesting about this interview is that he also mentioned that Ri-Ri was the one who pursued him…He was probably intimidated at first. No wonder she’s able to date so many guys, girlfriend’s not afraid to make the first move!

Josh Hartnett

From one Hollywood actor to another! Next up was former teen heartthrob Josh Hartnett. Rihanna admitted to dating the actor in November 2007 when she said, “I would be lying if I told you we were not more than just friends… I’ve fallen for him big time. ” She must fall pretty easily because this thing ended within two months!

Chris Brown

The most publicized relationship was with the one and only Chris Brown, and with good reason. The couple dated for over a year, and ended violently in February 2009 when Brown physically assaulted her. But of course, as most of you know, the two have recently reunited in more ways than one. Recording remixes together, going to the same parties, and well…hanging out from time to time (whatever that means). Though Chris has a new love, he and Rihanna have reportedly kept up…whatever it is they’re doing…and many folks seem to be thirsty for a reunion. Why, we’re not so sure…

Matt Kemp

Rihanna also seems to have a thing for athletes. She started dating L.A. Dodgers baseball player Matt Kemp in January 2010, shortly after the assault from Chris Brown. The two actually lasted for a whole year and were a very good looking couple. But reportedly, Rihanna just wasn’t feeling it, or feeling Kemp after a while. It was cute while it lasted, and we’re hoping Kemp is still on the market because he’s too fine!

Ryan Phillippe

Rihanna is rumored to have started dating Ryan Phillippe in December 2010, the ex-husband of actress Reese Witherspoon (and everybody’s crush after the movie Cruel Intentions back in the day). He was considered to be her rebound after things broke off with Matt Kemp. Phillippe reportedly attended Ri-Ri’s birthday party in February, and things fizzled out just as fast as she blew out her candles…perhaps she wished for a new boyfriend?

J.R. Smith

In May 2012, she was linked with NBA basketball player J.R. Smith. Reports of the two being seen together quickly surfaced, and the two were rumored to be “hanging out.” She had been seen sitting on his lap and chilling with the guard at club LIV. Smith, known for his legal troubles and bevvy of tattoos, definitely seemed like her “bad boy” type. However, homeboy wasn’t, because nothing has really come of the rumors an she’s still out in these streets pimpin‘…

Ashton Kutcher

From her shortest fling, to her most raunchy fling, this has got to be her most interesting hook–up of all. In March 2012, paparazzi caught Rihanna visiting Ashton Kutcher’s house alone at midnight…can you say booty call? This came only a few months after Kutcher went through a highly publicized divorce. When asked about it during media tours for her movie “Battleship,” she didn’t say it was true, and she didn’t say the rumors were false–in fact, she was just pissed that she was even being asked the questions. Whatever it was between them, it ended pretty fast as well, with Ri-Ri allegedly being dumped because Kutcher felt like she wanted publicity. But that doesn’t make much sense, this girl gets more publicity than most!


We’ve all seen the chemistry they had in the “What’s My Name” and “Take Care” videos. Nope, they’re not just really great actors…not too long ago, the two were spotted together at a Miami nightclub. Photo evidence shows the two holding hands, while other club goers claimed the two were dancing extremely close to each other all night. It doesn’t just start here. This comes a year after the two had already been rumored to be dating in 2011 for a short time. Clearly Ri had a strong effect on the guy, he’s discussed their “relationship” in a song “Fireworks,” and used to talk about her often in interviews. Sprung, much?

Meek Mill

This fling I can’t really wrap my head around, but whatever works for her! Rihanna and the Maybach Music Group rapper were said to be spending a lot of time together in Los Angeles, hanging out in the studio together, clubbing, and getting real acquainted. They’ve even publicly sent suggestive Tweets to one another. But we all know that whatever they had going on started some childish drama. The rapper, who was slated to appear on a track with Chris Brown, got on Twitter and claimed that the singer removed him from the song because of his affiliation with Ri-Ri. What came about was a string of random Tweets, with even Drake jumping in to say, “Oh Thats your ho? Thats our ho too LoL”

But no worries, Rihanna decided to throw in her two cents and drop the H-bomb too: “Cupid stay away from my hoes!!!!!!”

Whatever that means…

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