Everything about Rihanna’s romantic life from Chris Brown to A$AP Rocky

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Rihanna has frequently expressed her desire for a proper family life with a spouse and children. Over the years, she has spent her life with several well-known men, including a contentious affair with rapper Drake and a public liaison with singer Chris Brown, per PEOPLE. “Single life is so overrated,” the singer said on The Jonathan Ross Show back in 2012. “It sucks. I have had 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.”

1. Chris Brown

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Chris Brown was Rihanna’s first publicly known relationship. The pair, who met as teenagers, started to get cozy in 2008, and even though they denied all rumors that they were together, the media quickly caught wind of their romance. The relationship was beautiful at first, with the two spending time personally and collaborating professionally, but all of it changed in early 2009.

Brown assaulted Rihanna in a vehicle in February, just hours before their scheduled performance at the 2009 Grammy Awards. Brown was arrested on felony criminal threats charges after Rihanna contacted 911 and identified him as the aggressor; $50,000 bail was later posted. Brown admitted guilt. Following the incident, Rihanna admitted that she had “felt like an empty vessel” in an interview in October 2010. “I needed that wake-up call in my life,” she added. “That was the only way I would have gotten out of that relationship.”

2. Drake

Rihanna and Drake dated intermittently from 2009 through 2016. After she parted ways with Chris Brown, the two embarked on their first date.

Drake and RiRi were photographed in London in May 2014, holding hands. To congratulate Rihanna on receiving the MTV Michael Jackson Video Vanguard Award, Drake bought a billboard in August 2016. “She’s someone I’ve been in love with since I was 22 years old,” he said while presenting her with the award. At the afterparty, he “was literally shadowing her every movement and was just so affectionate and adoring the entire night,” a source told PEOPLE. However, the alleged couple split up in 2018, although no one has a reason why.

3. Matt Kemp

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Mutual friends arranged for Rihanna and Los Angeles Dodgers outfielder Matt Kemp to meet in November 2009. By January 2010, they were photographed becoming close while on vacation in Cabo San Lucas, Mexico, as things heated up swiftly. “They couldn’t keep their hands off of each other,” a source told PEOPLE. “They kept kissing while gazing out over the ocean.”

“I’m so happy. I feel really comfortable, and it’s so easy,” she opened up in June of that year. “I have such a chaotic life, but at the end of the day, that is just my peace. It keeps me sane, really, talking to him and talking to my family.”

However, the pair called it quits in December 2010.

4. Travis Scott

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Rapper Travis Scott and singer Rihanna were originally connected in late 2015 when they were photographed out together on various occasions, including a tattoo appointment, a fashion week afterparty, and other nights out in West Hollywood, California.

Rihanna was there for Scott’s performance at 1 OAK nightclub in Hollywood in October. “Once Travis finished his set, they were inseparable and all over each other,” an onlooker told PEOPLE. “It was cute!”

Beginning in February 2016, Scott served as Rihanna’s opening act on the North American leg of her Anti tour. Despite rumors of a love relationship swirling for months, the couple never confirmed it. Scott continued to date Kylie Jenner, with whom he eventually had two children.

5. Hassan Jameel

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In June 2017, Hassan Jameel, a Saudi businessman, was initially romantically associated with the Love on the Brain singer. Even though they hardly ever discussed their relationship in public, they weren’t afraid to go on dates. In July 2018, rumors of a breakup began to circulate when photos of Rihanna and Jameel arguing went viral.

In August 2019, the couple looked to be dating seriously after spending a “lovely dinner evening” with Monica Braithwaite Fenty, Rihanna’s mother, and her brother. In January 2020, Rihanna and Jameel called it quits on their relationship of over three years. A source told PEOPLE, “Their lives were too different and it was hard to maintain a relationship.”

6. A$AP Rocky

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When Rihanna and A$AP Rocky performed a remix of her song Cockiness (Love It) at the 2012 MTV Video Music Awards, fans first saw their connection. The two then began a fruitful business partnership and a strong friendship. Rihanna joined A$AP on tour and made an appearance in the Fashion Killa music video in 2013.

A$AP donned a black suit by Fenty, according to Elle, when the two walked the red carpet together at the British Fashion Awards in December 2019. The next month, Rihanna went single, and her burgeoning relationship with A$AP was officially announced in November 2020. They spent the holidays together in Barbados, where she is from. “They’ve been inseparable the past few weeks,” a source told PEOPLE in December. “It’s a new relationship, but they both seem very into it.”

A$AP was quite open about his affection for Rihanna in a May 2021 interview with GQ. “The love of my life,” he said when her name was brought up. “My lady.” He continued, “[Being in a relationship is] so much better. So much better when you get the One. She amounts to probably, like, a million of the other ones. I think when you know, you know. She’s the One.”