Entertainment Music Rihanna's Dating History: From Drake to A$AP Rocky After romances with rapper Drake and businessman Hassan Jameel, Rihanna began dating A$AP Rocky in 2020 and the couple is currently expecting their second baby together By Emy LaCroix Emy LaCroix Twitter Emy LaCroix is a contributing writer at PEOPLE. She has been working at PEOPLE since 2022. She previously worked as the deputy editor of Life & Style, In Touch, and Closer Weekly. People Editorial Guidelines Published on February 16, 2023 11:09 AM Share Tweet Pin Email Photo: Amy Sussman/WireImage Rihanna has always been open about wanting a partner and a family. "Single life is so overrated," the singer said on The Jonathan Ross Show in 2012. "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." She has shared her life with several famous men over the years, including a rocky relationship with singer Chris Brown and a high-profile romance with rapper Drake. Though she's dated many stars, A$AP Rocky has captured her heart. "A lot of guys have tried to sweep her off her feet, but A$AP actually managed to do it," an insider told PEOPLE in January 2022. "He's over-the-top romantic and sends her rooms full of flowers all the time. She's never felt this way before and this relationship has changed her." Later that year, Rihanna and A$AP welcomed their first child together, a son. And in February 2023, the singer revealed that she is currently pregnant with her second baby. Here's a look back at Rihanna's dating history. Chris Brown Christopher Polk/Getty Rihanna's first public relationship was with singer Chris Brown. The pair met as teenagers early on in their music careers and soon began collaborating on music. After Rihanna's "Umbrella" became a hit, Brown created its "Cinderella" remix, which he later performed on tour with the singer in 2008. In February 2008, the couple were spotted getting cozy at a Grammy Awards afterparty and at Rihanna's 20th birthday party, where Brown sang "Happy Birthday" to her. At the Grammys party, Brown told PEOPLE that they were "just friends," a sentiment that the pair repeated for the next few months. But in that time, they went on numerous dates, including to a Kanye West show, a summer trip to Barbados and a Sydney shopping spree. However, the following February, Brown assaulted Rihanna in a car hours before they were scheduled to perform at the 2009 Grammys. Rihanna called 911 and named Brown as her attacker; Brown was booked on felony criminal threats charges before posting $50,000 bail. "They've been fighting a lot lately," a source told PEOPLE at the time. "Lots of ups and downs. One second they're all lovey-dovey and then they're fighting like crazy." Brown pleaded guilty to the felony charges on June 22, 2009, and accepted a plea deal that included community labor, five years probation and domestic violence counseling, as well as a restraining order. Rihanna recounted details of the incident later that year. In October 2010, Rihanna shared that she had "felt like an empty vessel" following the assault. "I needed that wake-up call in my life," she added. "That was the only way I would have gotten out of that relationship." In 2011, a judge relaxed Brown's restraining order, allowing the former couple to speak to each other. The next year, Rihanna and Brown sparked reconciliation rumors when they collaborated on several songs together. Rihanna denied the rumors of a rekindled relationship to Oprah Winfrey, adding that she and Brown still loved each other. However, in January 2013, Rihanna confirmed their relationship and defended getting back together with Brown. "I decided it was more important for me to be happy and I wasn't going to let anybody's opinion get in the way of that," she said. "Even if it's a mistake, it's my mistake." Rihanna and Brown broke up for good in April 2013. Drake Rihanna and Drake in 2016. Kevin Mazur/WireImage Rihanna first met Canadian rapper Drake when he was an extra in her "Pon de Replay" music video in 2005. Though they started out as friends, their relationship turned romantic in May 2009 when the pair were spotted making out at a New York City bowling alley. In November, Rihanna told radio personality Angie Martinez that they were just friends — but the evening rang more sentimental to Drake, who later said he felt like "a pawn" and referenced their bowling date in his song "Fireworks." Despite their differences, the pair remained friendly and collaborated on Rihanna's 2010 song "What's My Name." They later performed the duet at the 2011 Grammys, and the steamy performance fueled speculation that there was more to their relationship. Later that year, Rihanna and Drake were seen spending time together in Montreal, and in 2012 Drake released "Take Care" featuring the Barbados-born singer. In 2014, his "ultimate fantasy," as he described Rihanna to Rolling Stone, joined him on several stops of his tour. But in 2015, Rihanna denied dating Drake to Vanity Fair, saying her "last real, official boyfriend was Chris Brown." Over the next few years, the two singers were periodically spotted together at parties, concerts and the like. Drake made a grand gesture in August 2016 by purchasing a billboard to congratulate Rihanna on winning the MTV Michael Jackson Video Vanguard Award. "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. In September 2016, they got matching shark tattoos, but by 2018, the "Umbrella" singer and Drake had ended their relationship. "We don't have a friendship now, but we're not enemies either," Rihanna said in an interview. While the duo shared some friendly online banter in March 2020, Rihanna covered up her shark tattoo with a crown in 2021. Matt Kemp Noah Graham/NBAE Rihanna and Los Angeles Dodgers outfielder Matt Kemp were introduced by mutual friends in November 2009. Things heated up quickly, and by January 2010, they were spotted getting cozy while on vacation in Cabo San Lucas, Mexico. "They couldn't keep their hands off of each other," a source told PEOPLE. "They kept kissing while gazing out over the ocean." A few months later, Rihanna confirmed her newfound romance in an interview with Ryan Seacrest. "He's my boyfriend," she said. "It's new, and it's fun, and it's nothing too serious, you know. I don't want anything that's going to take up so much of my energy and time right now in a bad way." Rihanna and Kemp continued to date through the summer. "I'm so happy. I feel really comfortable, and it's so easy," she told Elle in June. "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." By December 2010, however, the couple ended their relationship. Travis Scott Jean Catuffe/Getty Rihanna and rapper Travis Scott were first linked in late 2015, when they were spotted on several outings together, including a tattoo appointment, a fashion week afterparty and multiple nights out in West Hollywood, California. In October, Rihanna attended Scott's set at Hollywood nightclub 1 OAK. "Once Travis finished his set, they were inseparable and all over each other," an onlooker told PEOPLE. "It was cute!" Scott opened for Rihanna on the North American leg of her Anti tour beginning in February 2016. Despite months of circulating rumors, the pair never acknowledged a romantic relationship between them. Scott went on to date and welcome two children with Kylie Jenner. Hassan Jameel Rihanna, Hassan Jameel. Allen Berezovsky/Getty Images The "Love on the Brain" singer was first romantically linked to Saudi businessman Hassan Jameel in June 2017. Though the couple rarely spoke publicly about their relationship, they weren't shy about going on dates. Rumors of a split spread in July 2018 when Rihanna and Jameel were photographed during a heated conversation, but the singer shut them down with a meme on Instagram. In June 2019, actress Sarah Paulson spoke to the Grammy-winning artist for Interview magazine. "Are you in love?" Paulson asked, to which Rihanna replied, "Of course I am." The Fenty founder added that she was prioritizing her personal life over her career. "I got into a new relationship, and it matters to me," she said. "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." The relationship appeared to take a serious turn in August 2019: Rihanna and Jameel spent a "lovely dinner evening" with her brother and her mom, Monica Braithwaite Fenty. "They all stayed a good few hours of the night until dark," a source told PEOPLE. Rihanna and Jameel's romance ended in January 2020 after nearly three years together. A source told PEOPLE, "Their lives were too different and it was hard to maintain a relationship." A$AP Rocky A$AP Rocky and Rihanna. Rich Fury/Getty Fans first noticed chemistry between Rihanna and A$AP Rocky when they performed a remix of her song "Cockiness (Love It)" at the 2012 MTV Video Music Awards. From there, the pair kicked off a positive working relationship and a close friendship. In 2013, A$AP toured with Rihanna and she appeared in his "Fashion Killa" music video. In June 2018, they sat together in the front row for the Louis Vuitton Menswear show at Paris Fashion Week. In December 2019, the pair hit the red carpet together at the British Fashion Awards — A$AP wore a black suit by Fenty, according to Elle. Rihanna became single within the next month, and in November 2020, her and A$AP's budding romance was confirmed. The pair spent the holidays together in her home country of Barbados. "They've been inseparable the past few weeks," a source told PEOPLE in December. "It's a new relationship, but they both seem very into it." In May 2021, A$AP made his feelings for Rihanna extremely clear in an 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 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." The longtime friends made their red carpet debut as a couple at the 2021 Met Gala. On Jan. 31, 2022, Rihanna and A$AP revealed they were expecting their first baby with a photo shoot showing off her baby bump. In April 2022, a viral tweet accused A$AP of cheating on the pregnant "Diamonds" singer with designer Amina Muaddi. The designer quickly set the record straight and insisted that the "vile" reports were entirely unfounded. Trouble continued to plague A$AP that month: He was arrested and detained in L.A. in connection with a November 2021 shooting. He was charged with felony assault with a deadly weapon and his bail was set at $550,000. He was released from jail later that day; he pleaded not guilty to the charges in August. In May, Rihanna and A$AP welcomed their first child, a baby boy. "Rihanna is doing well," a source told PEOPLE. "They are very excited to be parents. Rihanna is already a wonderful mom." Now, Rihanna and A$AP are expecting their second baby together after the singer debuted her baby bump during her Super Bowl Halftime show performance on Feb. 12, 2023. A$AP was on the field in Arizona to watch Rihanna take the stage for the first time in several years.