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The Complete Rihanna Boyfriend List: Chris Brown, Shia LaBeouf, Drake, Big Sean And More

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Rihanna
(Photo : Neilson Barnard/Getty Images) The Complete Rihanna Boyfriend List

Rihanna’s dating life always keeps us buzzing - especially thanks to her habit of going on-again, off-again with exes like Chris Brown and Drake. After splitting from Drake earlier this year, Rihanna is now apparently single - but was recently spotted flirting with Big Sean after his split from Naya Rivera.

Read on to see everyone Rihanna has dated - or even been linked to! Tell us your favorite BF in the comments below.

 

Negus Sealy (2003, 2011)

(Photo : Twitter/Negus Sealy)

Rihanna’s first boyfriend Negus Sealy, who she dated when she was 15, was linked to her again in 2011 when they were spotted dirty dancing in Barbados. Negus said, “I am so lucky to have spent so much time with her and will always consider her to be a closer personal friend .I value her so much because she has been pretty much been straight up and real with me from the beginning. But right now she doesn’t have time for anything serious with any guy.”


Jay-Z (2005-2014) 

(Photo : Larry Busacca/Getty Images for NARAS)

Rihanna has been linked to Jay-Z ever since he discovered her in 2005! Both stars have always insisted that their relationship is strictly professional and that Jay-Z is Rihanna’s mentor.

 

 

Chris Brown (2005-2013)

(Photo : Christopher Polk/Getty Images for NARAS)

Rihanna and Chris were first linked back in 2005, but they insisted they were just friends; they confirmed the relationship in 2008, and broke up after Chris was arrested for domestic violence against Rihanna in 2009. They were rumored to have rekindled their romance in early 2012, but didn’t confirm it until almost a year later. In May 2013, Chris confirmed that he and Rihanna had split - apparently for good.


Shia LaBeouf (2007)

(Photo : Vittorio Zunino Celotto/Getty Images)


Rihanna and Shia were linked back in 2007 when she wrote the theme song for his movie “Disturbia.” Shia later confirmed that they went on one date, saying, “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.”


Josh Hartnett (2007)

(Photo : Scott Gries/Getty Images)


Also in 2007, Rihanna was linked to mid-2000s heartthrob Josh Hartnett. Rihanna later denied the rumors, saying, "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?"


Justin Timberlake (2009-2010)

(Photo : David Becker/Getty Images)


Rihanna and JT were rumored to be secretly dating in late 2009 and early 2010. Neither star commented, but the rumors were short-lived.


Rashard Lewis (2009)

(Photo : Chris Trotman/Getty Images)


Rihanna was spotted out with Rashard Lewis in 2009, but the rumors only lasted a few weeks.


Drake (2009-2014)

(Photo : Kevin Winter/Getty Images)


Another on-again, off-again relationship, Drake was first linked to Rihanna shortly after she split from Chris Brown. They’ve stayed friends ever since, sparking countless dating rumors throughout the years. Most recenlty, they appeared to be about to make it official in March but apparently split in May - though neither ever confirmed the rumors.


Matt Kemp (2009, 2013)

(Photo : Kevork Djansezian/Getty Images)


Rihanna and Matt dated for about a year beginning in late 2009; during that time, Rihanna mentioned her boyfriend in interviews but never named Matt. They were briefly linked again in 2013.


Ryan Phillippe (2010-2011)

(Photo : Rob Kim/Getty Images)


Rihanna and Ryan were rumored to be hooking up in late 2010 and early 2011. Asked if she was dating Ryan, Rihanna said, "No no no, I hate to burst your bubble, but no. I am dating girls, I am just kidding!”


Travis Barker (2011)

(Photo : Michael Buckner/Getty Images for BET)

 

 

Around the same time Rihanna was linked to Ryan, rumors also placed her with Blink-182 drummer Travis Barker. However, the rumors were short-lived and neither commented.


Dudley O’Shaughnessy (2011-2013)

(Photo : Ben Pruchnie/Getty Images)


When Rihanna cast model Dudley O’Shaughnessy in her “We Found Love” music video, the sexy costars were rumored to have taken their relationship offscreen as well. They were linked again after Rihanna split fro Chris Brown in 2013.


Ashton Kutcher (2012)

(Photo : Frazer Harrison/Getty Images)


Rihanna and Ashton were rumored to have had a short fling in 2012, but she told reporters, “Wow, how disappointing was that question. I’m happy and I’m single, if that’s what you’re really asking.”


Darren McFadden (2012)

(Photo : Ezra Shaw/Getty Images)


Rihanna was briefly linked to football star Darren McFadden, however, the rumors went nowhere.


JR Smith (2012-2013)

(Photo : Stephen Lovekin/Getty Images)


Rihanna and JR Smith were linked in 2012 and 2013, however, neither confirmed the rumors - although Rihanna trashed the Knicks on Instagram after their apparent breakup.


Big Sean (2014)

(Photo : Jason Merritt/Getty Images for Trevor Project)


Recently, Rihanna and Big Sean were reportedly spotted flirting at a party. We’ll see if these rumors go anywhere!

 

 

 

 

 

 

 

 

 

 

 

 

 

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