Rihanna has been dating her longtime friend A$AP Rocky since 2020, and the couple are now expecting their first child together.
Before her romance with A$AP, the Barbadian beauty dated a host of famous faces – including Drake, Travis Scott and Lewis Hamilton.
We’ve taken a look back at the singer’s dating history, including confirmed romances and rumoured flings.
Take a look:
Shia LaBeouf
Shia LaBeouf went on a date with Rihanna in 2007.
Speaking to Playboy about their brief romance, the 35-year-old Transformers star said: “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.”
Chris Brown
Rihanna and Chris Brown dated on-off for a few years before their romance took a nasty turn in 2009, when he physically assaulted her on the way home from a Grammy’s party.
The R&B singer was ordered to serve five years of probation, community service and counselling for domestic violence.
Speaking to Oprah about her relationship with Chris in 2012, Rihanna said: “We’ve been working on our friendship again. Now we’re very very close friends.”
“We’ve built up a trust again, and that’s – we love each other and we probably always will. And that’s not something we’re ever going to change. That’s not something you can shut off, if you’ve ever been in love.
“I think he was the love of my life. He was the first love. And I see that he loved me the same way… it’s not even about us being together. I truly love him. So the main thing for me is that he’s at peace. I’m not at peace if he’s a little unhappy, or he’s still lonely.”
Matt Kemp
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After splitting from Chris, Rihanna was linked to professional baseball played Matt Kemp.
In 2010, Matt told Us Weekly: “Yeah! That’s my girl! She’s just a fun person. I love to be around her.”
The relationship didn’t last long due to the songstress’ busy schedule.
Ashton Kutcher
Rihanna was linked to actor Ashton Kutcher in 2012.
The S&M singer sparked romance rumours when she was papped leaving his $10 million bachelor pad in the middle of the night, and it was reported at the time that the pair had an eight-week fling.
A source told The Sun at the time: “The flirting began as soon as Rihanna and Ashton met and swapped numbers. That moved onto texts and arranging to meet…. They are two single people having a fling, so thought it would be best to meet in secret.”
“Rihanna has told friends he’s funny and cute. Both of them love a good time and think they’re too busy for anything serious just yet.”
Karim Benzema
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Rihanna reportedly reached out to soccer player Karim Benzema during the 2014 World Cup, and the pair struck up a romance.
They were spotted hanging out together in New York in 2015, with an insider telling E! News that Karim was a good match for the Diamonds singer because he understood her hectic schedule and gave her “the space she needs.”
The couple reportedly split because Rihanna was still hung up on her ex Chris Brown.
Leonardo DiCaprio
Rihanna was spotted cosying up to Oscar-winning actor Leonardo DiCaprio in 2015 at a nightclub in Paris, the rumoured couple were dubbed ‘Lihanna’ and ‘Rihcaprio’.
A source told Us Weekly at the time that while Leo thought Rihanna was “incredibly hot,” neither one of them were “looking for a relationship”.
The pair were spotted hanging out again at Coachella the following year, but nothing ever came from it.
Lewis Hamilton
In August 2015, Rihanna and Formula One race car champion Lewis Hamilton were spotted vacationing in her native Barbados.
Days earlier, the pair were also seen looking flirtatious at the Grand Kadooment Day carnival.
Lewis insisted he and the songstress were “just friends” at the time, telling E! News: “You know, I’ve known Ri for a long time. We’ve been friends for a while. We get to hang out every now and again.”
Travis Scott
Travis Scott and Rihanna were spotted kissing at a New York Fashion Week party in September 2015.
In his Complex cover story, Travis called Rihanna “creative, inspiring and a muse”.
Shortly afterwards, Travis was linked to Kylie Jenner, who he is now expecting his second child with.
Drake
Rihanna and Drake reportedly dated on-and-off from 2009 to 2016.
Speaking at the MTV Video Music Awards in 2016, Drake said Rihanna was “someone I’ve been in love with since I was 22.”
But two months later, the couple called it quits due to conflicting schedules.
In 2018, Rihanna told Vogue magazine that she and Drake were no longer friends, but were “not enemies either.”
Hassan Jameel
Rihanna and Hassan Jameel have split after nearly 3 years of dating, @UsWeekly reports. pic.twitter.com/WnBXSB0iP5
— Pop Crave (@PopCrave) January 17, 2020
In 2017, Rihanna started dating Saudi billionaire Hassan Jameel.
The couple were spotted at several events together, but kept their romance mainly out of the limelight.
In January 2020, the couple called it quits after nearly three years together.
A source told PEOPLE magazine at the time: “Their lives were too different, and it was hard to maintain a relationship.”
A$AP Rocky
Rihanna was romantically linked to her longtime friend A$AP Rocky in 2020, following her split from Hassan Jameel.
A$AP, whose real name is Rakim Athelaston Mayers, was Rihanna’s opening act during the US part of her Diamonds World Tour in 2013.
The rapper also featured on the Barbadian beauty’s 2011 track ‘Cockiness’, and teamed up with the songstress for a Fenty Skin campaign.
The couple finally confirmed their romance in May 2021, with A$AP calling Rihanna “the love of my life”.
He told GQ magazine: “[Relationships are] so much better when you got the One. She amounts to probably, like, a million of the other ones. I think when you know, you know. She’s the One.”
On Monday, the couple revealed they are expecting their first child, with Rihanna debuting her baby bump in NYC.
more photos of rihanna and asap rocky in nyc🤍 pic.twitter.com/QsWA4UrdZx
— ✨ (@PRADAXBBY) January 31, 2022
