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Rihanna and Drake

Rihanna’s Most Famous Romantic Connections

Gettyimages | Kevin Mazur
By Jordan White

Rihanna, 32, has never been too vocal about her personal life. Her most publicized relationship was with Chris Brown who she started dating in 2007.

In 2009, Brown was charged with assault towards the ‘Needed Me’ singer.

In 2013, years after the incident, Brown and Rihanna started dating again while he was still under probation for domestic violence. Their romance ended, for the second time, that same year.

And while C Breezy is probably the ex most people talk about, Rihanna has dated some very famous men. Keep scrolling to see who we’re talking about!

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1. Shia LaBeouf

Shia LaBeouf
Gettyimages | Rich Fury

Rumors of a relationship started in the summer of 2007 when Rihanna and Shia LaBeouf were spotted eating dinner together in Beverly Hills.

At the time, neither Rihanna or LaBeouf confirmed whether the two were strictly friends or something more. However, two years later, the ‘Transformers’ star revealed what really went down.

While filming, LaBeouf got a message from the singer and the two agreed to meet up.

‘It never got beyond one date,’ he told Playboy. ‘The spark wasn't there. We weren't passionate about each other in that way, so we remain friends.’

2. Matt Kemp

Matt Kemp
Matt Kemp/Instagram

In 2010, Rihanna dated LA Dodgers baseball player, Matt Kemp, after her relationship with Chris Bown ended.

The two were together for about a year, and during their relationship, they couldn’t help but gush about the other.

‘She's just a fun person. I love to be around her,’ Kemp said.

Sadly, they split in December 2019. And according to an insider, the relationship wasn’t that serious.

‘It was never as serious as it looked. It was always just [about] having fun,’ a source told Us Weekly.

3. Leonardo DiCaprio

Leonardo DiCaprio
Leonardo DiCpario/Instagram

The pair reportedly starting dating in 2015. Supposedly, DiCaprio even helped plan the singer's 27th birthday.

That year, they were seen together several times, adding fuel to the relationship rumors.

However, Rihanna seemed to deny the rumors during an interview with Hello!

When asked, ‘How does Rihanna DiCaprio sound to you?’ Rihanna responded with, ‘It sounds to me like you should stay away from the blogs because they will screw you every time.’

She continued, 'I’m so busy right now that I just don’t have a lot of time to offer to a man so it wouldn’t even be fair to be thinking of pulling somebody else into this life. But if I did, he would have to be man enough to live with my schedule and not get scared.'

4. Drake


Rihanna and Drake reportedly had an on and off-again relationship between 2009 to 2016.

After she split with Brown, Rihanna was seen making out with the ‘God’s Plan’ singer.

But their relationship was never steady for long.

In 2016, they were rumored to be dating again. The pair even made it official, with matching shark tattoos. But they split (again) later that year.

A source told Us Weekly, 'She [Rihanna] doesn’t want to be held down. They will always be close. If they end up together, it could happen, but not now.’

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