Inside Rihanna’s love life – millionaire ex, Hollywood hunk and Chris Brown controversy

Before settling with rapper ASAP Rocky and welcoming a baby boy, RiRi found love in a hopeless place with several men, but things didn’t work out – take look inside the music superstar’s love life

Music superstar Rihanna has finally found the man who makes her feel like the only girl in the world: A$AP Rocky.

After months of dating rumours and years of being at each other’s side, the power music couple made their romance official in 2021.

With their relationship going from strength to strength, Rihanna and ASAP recently welcomed an adorable baby boy in May last year.

Before RiRi settled down with the rapper though, she found love in a hopeless place with several men – but things didn’t seem to work out.

From a short-lived fling with an A-list rapper to an alleged smooch-fest with a Hollywood star – the Daily Star takes a look inside pop superstar Rihanna’s love life.

Chris Brown

Rihanna first started dating Chris in the later 2000s
Rihanna first started dating Chris in the later 2000sThe Love On The Brain hitmaker was in a very public and controversial relationship with Chris Brown from 2007 to 2009.Their romance hit the headlines when he was arrested for allegedly attacking Rihanna in 2009 before the Grammy awards.

Chris pleased not guilty in April 2009 to one count of ᴀssault and one count of making criminal threats stemming from the incident – which took lace on February 8.

He later pleaded guilty to the felony and accepted a plea on June 2022 the same year. He was sentenced to five years of probation in addition to community service and domestic violence counselling.

Rihanna and Chris rekindled their romance for a short period in 2013 though, despite Chris still being under probation for the incident.

Matt Kemp

Rihanna moved onto Matt after splitting from Chris
Rihanna moved onto Matt after splitting from Chris (Image: Getty Images)

RiRi dated professional baseball player Matt Kemp back in 2010 for just under a year, from January-December.

The two called it quits because Matt, who plays for the Miami Marlins, couldn’t cope with Rihanna’s busy schedule.

“He just can’t keep up with her crazy travel schedule,” a source told US Weekly.

“Matt’s sick of always following after her like a puppy dog all over the world. He wants something more normal.”


Rihanna and Drake have apparently had an on-off relationship for years
Rihanna and Drake have apparently had an on-off relationship for years (Image: WireImage)

Rihanna has done plenty of collaborating with Canadian rapper Drake over the years, on hits like Work and What’s My Name?

And it appears the two were more than just music pals as they reportedly had an on/off relationship between 2009-2016.

Drake even famously professed his love for Rihanna on stage at the MTV Video Music Awards in 2016.

“She’s someone I’ve been in love with since I was 22 years old,” he gushed. “She’s one of my best friends in the world.”

Travis Scott

In 2015, Rihanna was linked with Travis
In 2015, Rihanna was linked with Travis (Image: Penske Media via Getty Images)

Back in 2015, the FENTY founder and Travis Scott has a short-lived romance, which apparently came to an end after their relationship fizzled out.

The two were spotted together at New York Fashion Week in 2015, with an insider claiming: “Travis and Rihanna are dating.”

Speaking to E! Online, they added: “It’s already very serious. He’s very into her.”

However, shortly after it was reported that their relationship had ended because Travis had become too “needy” for RiRi, as Urban Izlands reports.

Leonardo DiCaprio

Rihanna was rumoured to have shared a kiss with Leonardo
Rihanna was rumoured to have shared a kiss with Leonardo (Image: Getty Images North America)

The internet went wild in 2016 after Paige Six reported Rihanna and Hollywood star Leonardo Dicaprio were spotted kissing.

Apparently, they were seen getting cosy at a nightclub in Paris called club L’Etoile.

Their romance was never confirmed and sources at the time said the two A-listers were “just friends.”

“Rihanna came in with Cara Delevingne. She congratulated Leo and kissed him on the cheek. They didn’t hang out there, though, and left separately shortly after,” an insider told the Mirror.

Hᴀssan Jameel

Rihanna dated businessman Hᴀssan Jameel for three years
Rihanna dated businessman Hᴀssan Jameel for three years (Image: 247PAPS.TV / Splash News)

Rihanna dated Saudi businessman Hᴀssan Jameel back in January 2017 and the two were together for three years.

The following year, she opened up to Vogue about her love life, revealing that she was in a relationship – but didn’t want to give too much away.

“Yeah, I’m dating. I’m actually in an exclusive relationship for quite some time, and it’s going really well, so I’m happy.”

The two called it quits in January 2020 though.

A source told People that “their lives were too different and it was hard to maintain a relationship.”

Asap Rocky

Rihanna is currently loved up with ASAP Rocky
Rihanna is currently loved up with ASAP Rocky (Image: Getty Images for Fenty Beauty &)

Everyone’s favourite music couple first confirmed their relationship in May 2021.

But Rihanna and ASAP have known each other for a long time since they collaborated together on their track Fashion Killa’in 2013.

In that same year, he jumped on a remix for her track Cockiness (Love It) and opened up for her on her Diamonds world tour.

In May last year, the rapper finally confirmed their romance as he raved about RiRi to GQ, calling her “the love of my life” and “the One”.

He added: “She amounts to probably, like, a million of the other ones. I think when you know, you know.”

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