Speaking to Ellen DeGeneres in 2011, Rihanna admitted that being labeled the ‘sexiest woman alive’ can make her ‘intimidating’ to men — but she was looking for guys who step up into a traditionally masculine role.’

‘I like men who are more aggressive but mysterious,’ she said. ‘But I like a man to be very sure. I like them to be sure of themselves and know that you’re the man, I’m the lady, and the only way for us to make this work is if we play our roles. I can’t really be the man for you.’

She seems to have found quite a few men who’ve fit the bill over the years.

Rihanna dated Chris Brown from 2008 to 2009, then again from 2012 to 2013

Chris Brown

Rihanna’s relationship with the singer is one of her most well-remembered.

The pair met in 2005 but weren’t officially linked as together until 2008, when they were seen together at the Grammys and kissing at her 21st birthday party.

But in 2009, fans were shocked when news leaked that Chris had beaten Rihanna, and leaked police photos showed her with black eyes and bruises. He was arrested and charged with felony battery, to which he pleaded guilty and was sentenced to five years probation.

‘I needed that wake-up call in my life,’ Rihanna later tole Marie Claire UK. ‘I needed a turning point, and that’s what God was giving to me. All [of] this terrible stuff they say to you, it breaks you down.’ 

Rihanna filed a restraining order at the time, but she eventually forgave him, dropping the restraining order in 2011 and getting back together with him in 2012 — when she described their relationship as ‘true love’ in 2012. 

‘It took me a long time. I was angry for a long time. I was resentful, I held a grudge. I was dark. I was angry. It was coming out in my music and my clothes and my attitude. I didn’t like that feeling. It was heavy,’ she said.

They split again in 2013.  

Rihanna had a year-long relationship with LA Dodgers star Matt Kemp for the length of 2010

Matt Kemp 

While split from Chris Brown, Rihanna had a year-long relationship with LA Dodgers star Matt Kemp for the length of 2010. 

She gushed about the relationship in several interviews, telling Marie Claire UK: ‘I feel like I smile for real this time. The smiles come from inside, and it exudes in everything I do. People feel my energy is different. When I smile they can tell that it’s pure bliss and not just a cover up.’

But after splitting in December of that year, she told Vogue: ‘I just let it go. I don’t ever want to have to depend on a relationship. I think it’s a really special thing to find love. It’s beautiful. Nothing can match it, but I want to make sure I find other things in life that I love — besides love.’ 

Rihanna and Drake met in 2005 and famously dated on and off over the years (pictured in 2016)

Drake 

Rihanna and Drake met in 2005 and famously dated on and off over the years as they worked together on songs including Work, Take Care, and What’s My Name. 

During that time, Drake repeatedly gushed about Rihanna to different news outlet, describing her as his ‘ultimate fantasy.’

In 2016, he introduced her at the VMAs with effusive praise, saying: ‘We love the videos, which change their artistic vision from year to year. But most of all, we love the woman who hasn’t changed since day one. She’s someone I’ve been in love with since I was 22 years old, she’s one of my best friends in the world. All my adult life, I’ve looked up to her even though she’s younger than me. She’s a living, breathing legend in our industry,’ he said.

But it seems that RiRi wasn’t a fan of being built up that way, and told Vogue years later that ‘waiting through that speech was probably the most uncomfortable part. I don’t like too many compliments; I don’t like to be put on blast. 

‘We don’t have a friendship now, but we’re not enemies either. It is what it is,’ she said.

Rihanna and Leo were rumored to have hooked up a few times (pictured in 2016)

Leonardo DiCaprio

Rihanna and Leo were rumored to have hooked up a few times, first in February 2015 — when they reportedly spent Valentine’s Day weekend together.

Then, in 2016, they were spotted together at Intrigue Night Club’s grand opening at Wynn Las Vegas.

Neither confirmed that they had dated.

Rihanna also reportedly dated Travis Scott in 2015

Travis Scott

Rihanna also reportedly dated Travis Scott in 2015, with the rumors fueled by sightings of Rihanna at his concerts.

But the relationship appeared to be confirmed by a story in the December 2015/January 2016 issue of Complex. Writer Lawrence Schlossman said that Travis had missed their interview because he was ‘holed up with Rihanna, his recently rumored love interest/girlfriend/friend-with-benefit.’

In 2020, Schlossman said on his podcast that he was never supposed to reveal that Travis and Rihanna were together. 

‘It’s because Rihanna’s like, “Don’t tell anyone that I’m smashing Travis Scott, please,”‘ he said. 

Rihanna and Saudi Arabian businessman Hassan Jameel got together in 2017 and split by early 2020

Hassan Jameel

Rihanna and Saudi Arabian businessman Hassan Jameel got together in 2017. They were first spotted getting dinner together in November of that year, and in 2018 took a trip to Mexico together.

In 2019, she told Interview: ‘I got into a new relationship, and it matters to me. It was like, “I need to make time for this.” Just like I nurture my businesses, I need to nurture this as well. I’ll shut things down for two days, three days at a time. 

‘On my calendar we now have the infamous “P,’ which means personal days. This is a new thing.’

She spoke again about him later that year, telling Vogue: ‘I’m actually in an exclusive relationship for quite some time, and it’s going really well, so I’m happy.’ 

But things soured, and news that they split broke in January 2020. 

Though their romantic relationship is only a couple of years old, Rihanna and A$AP Rocky have known one another for a decade (pictured at the 2021 Met Gala)

A$AP Rocky

Though their romantic relationship is only a couple of years old, Rihanna and A$AP Rocky have known one another for a decade.

In 2012, he was featured in a remix of Rihanna’s song ‘Cockiness (Love It),’ and he joined her Diamonds World Tour as an opening act in 2013.

They remained friends over the years, even attending a Louis Vuitton show together in 2018 and the British Fashion Awards in 2019, among other events.

But when Rihanna and Hassan split in January 2020, rumors started to swirl that she and Rocky were together.

While they didn’t confirm that they were together, Rocky joined Rihanna to promote Fenty Skin in August 2020, and they were spotted out together that December, with reports that they were ‘inseparable.’ 

Rocky confirmed the relationship in May 2021, telling GQ that Rihanna is ‘the love of my life.’

‘I think when you know, you know. She’s the one,’ he said.