Rihanna has dated hip-hop legends like Drake and ASAP Rocky

Rihanna has consistently expressed her desire for companionship and a family. On The Jonathan Ross Show in 2012, she remarked, "Being single is vastly overrated. It sucks. I have such incredible experiences in my life. You don't want to live your life and then meet someone. You want to share your life with someone." Throughout the years, she's been involved with various well-known figures, such as a turbulent relationship with singer Chris Brown and a widely publicized romance with rapper Drake. Despite her history with multiple celebrities, it's A$AP Rocky who finally won her lasting affection.

Chris Brown

Arguably her most public relationship till now, Rihanna was romantically involved with Chris Brown from 2007 to 2009. Their breakup stemmed from a distressing event where Brown physically assaulted Rihanna, as per InStyle. After parting ways, they briefly reunited in 2013, only to separate shortly after. Despite their split, Chris has consistently expressed his affection and backing for his former partner, occasionally leaving heart emojis on her Instagram posts.

Matt Kemp

Rihanna was in a relationship with the pro baseball player for nearly a year, from January to December 2010, after breaking up with Chris. Matt, a Miami Marlins player, ended the relationship with the Savage X Fenty star because her schedule seemed to overwhelm him. A source shared with US Weekly, stating: "He just can't keep up with her crazy travel schedule. Matt's sick of always following after her like a puppy dog all over the world. He wants something more normal."

Lewis Hamilton

Lewis Hamilton and Rihanna have frequently been spotted in each others' company. While speculation about a romantic connection has circulated, Hamilton had to clarify in 2015, saying to E!: "I've known Ri for quite some time. We've been friends for a good while. We catch up every now and then."

Drake

Rihanna and Drake were said to have had a fluctuating romantic connection from 2009 to 2016. It led to some great creative collaborations, like hit songs 'Work', 'What's My Name', and 'Take Care'. Their bond, however, took a downturn, and Rihanna notably mentioned in a 2018 Vogue interview that their friendship had faded. She stated, “We don’t have a friendship now, but we’re not enemies either. It is what it is.” Nevertheless, they seemed to have reconciled as she was present at his 33rd birthday celebration in October 2019, as per CapitalFM.

Travis Scott

Travis Scott and Rihanna briefly dated in 2015, but their relationship hit a rough patch reportedly due to overwhelming circumstances for Rihanna. They were initially spotted together during New York Fashion Week that year, with an insider informing E! Online: "Travis and Rihanna are dating, officially. It's already very serious. He's very into her." However, their romance quickly faded away, with reports suggesting that the connection between Riri and the rapper, who shares a child with Kylie Jenner, didn't last long.

Hassan Jameel

Rihanna ended her three-year relationship with Hassan Jameel in January 2020. Despite their limited public appearances, the split was unexpected for fans, especially since she had confirmed her love for him in October 2019 by saying she was "of course" in love with her partner, as per Elle.

A$AP Rocky

Rihanna and A$AP Rocky forged a tight bond after teaming up on their song 'Fashion Killa' back in 2013, the same year he put his spin on her track 'Cockiness (I Love It)' and joined her on the Diamonds World Tour. Despite constant speculation about their relationship, it wasn't until May 2021 that he finally acknowledged their romance. But their public appearances together, like at the British Fashion Awards in December 2019 and her support at his concert in Sweden, had already fueled 'couple rumors' about them by then. A$AP has now referred to his partner as "the one," as per PEOPLE magazine.