Rihanna's romances, including Hassan Jameel, Chris Brown, Drake, and more of her romantic history

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Rihanna has, as she sings, found love in a hopeless place — and more than once. The “Love on the Brain” singer — who turns 30 on Feb. 20 — has romanced musicians, athletes, and singers, a number of whom are famous themselves. Take a look back at the notable loves of the star’s life so far.

<p>The rapper and Rihanna have <a href="http://www.cosmopolitan.com/entertainment/celebs/a63543/drake-rihanna-relationship-timeline-love-dating-aubrih-forever/" rel="nofollow noopener" target="_blank" data-ylk="slk:a complicated history" class="link rapid-noclick-resp">a complicated history</a>, going back years. They had a short-lived romance in 2009 — a little too short for Drake — which prompted him to tell the <i>New York Times</i> that he felt used by Rihanna. (He <a href="http://www.mtv.com/news/1641715/drake-explains-his-comments-about-rihanna/" rel="nofollow noopener" target="_blank" data-ylk="slk:later clarified" class="link rapid-noclick-resp">later clarified</a> that he didn’t mean for his comments to come across as negative.) They continued to be flirty together — both on and off the stage — and Rihanna ex Chris Brown seemed to be at war with Drake for a while. By 2016, Drake and RiRi seemed like they might be dating again, with her kissing him at his concert in full view of everyone and his gushing about her while <a href="https://www.yahoo.com/entertainment/watch-drake-present-video-vanguard-001329323.html" data-ylk="slk:presenting;outcm:mb_qualified_link;_E:mb_qualified_link" class="link rapid-noclick-resp newsroom-embed-article">presenting</a> her with the Video Vanguard Award at the 2016 MTV VMAs. “She’s someone I’ve been in love with since I was 22 years old,” he said. Think they’ll ever get back together? (Photo: Kevin Mazur/WireImage) </p>
Drake

The rapper and Rihanna have a complicated history, going back years. They had a short-lived romance in 2009 — a little too short for Drake — which prompted him to tell the New York Times that he felt used by Rihanna. (He later clarified that he didn’t mean for his comments to come across as negative.) They continued to be flirty together — both on and off the stage — and Rihanna ex Chris Brown seemed to be at war with Drake for a while. By 2016, Drake and RiRi seemed like they might be dating again, with her kissing him at his concert in full view of everyone and his gushing about her while presenting her with the Video Vanguard Award at the 2016 MTV VMAs. “She’s someone I’ve been in love with since I was 22 years old,” he said. Think they’ll ever get back together? (Photo: Kevin Mazur/WireImage)

<p>Rihanna’s current boyfriend isn’t an actor or an athlete. Saudi billionaire Jameel is an executive at his family’s company, Abdul Latif Jameel. As usual, Rihanna has kept the facts about her relationship to herself, but she did <a href="https://www.yahoo.com/entertainment/rihanna-parties-rumored-beau-hassan-171919804.html" data-ylk="slk:bring Jameel as her date;outcm:mb_qualified_link;_E:mb_qualified_link" class="link rapid-noclick-resp newsroom-embed-article">bring Jameel as her date</a> to a Grammys after-party in February. (Photo: Abdul Latif Jameel) </p>
Hassan Jameel

Rihanna’s current boyfriend isn’t an actor or an athlete. Saudi billionaire Jameel is an executive at his family’s company, Abdul Latif Jameel. As usual, Rihanna has kept the facts about her relationship to herself, but she did bring Jameel as her date to a Grammys after-party in February. (Photo: Abdul Latif Jameel)

<p>The <i>Transformers</i> star was spotted dining with RiRi in Beverly Hills in June 2007, but he only confirmed in 2009 that, yes, they had been on a date. Turns out she called him up out of the blue. “It never got beyond one date,” LaBeouf told <i>Playboy</i> (<a href="http://www.mtv.com/news/1611591/shia-labeouf-opens-up-about-his-one-date-with-rihanna/" rel="nofollow noopener" target="_blank" data-ylk="slk:via MTV" class="link rapid-noclick-resp">via MTV</a>). “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.” (Photo: J. Merritt/WireImage) </p>
Shia LaBeouf

The Transformers star was spotted dining with RiRi in Beverly Hills in June 2007, but he only confirmed in 2009 that, yes, they had been on a date. Turns out she called him up out of the blue. “It never got beyond one date,” LaBeouf told Playboy (via MTV). “The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.” (Photo: J. Merritt/WireImage)

<p>The “No Air” singer is Rihanna’s most infamous ex. They went public with their relationship in 2008, and he was spotted traveling home with her to Barbados. In February 2009, Brown assaulted Rihanna following a pre-Grammy party, for which he was sentenced to five years of probation and 1,400 hours of labor. Still, they were <a href="https://www.usmagazine.com/celebrity-news/news/rihanna-explains-why-she-got-back-with-chris-brown-after-assault-2015610/" rel="nofollow noopener" target="_blank" data-ylk="slk:photographed back together" class="link rapid-noclick-resp">photographed back together</a> in December 2012 and reportedly ended their relationship again in summer 2013. “I don’t hate him. I will care about him until the day I die,” Rihanna told <i>Vanity Fair</i> in November 2015. (Photo: Christopher Polk/Getty Images for NARAS) </p>
Chris Brown

The “No Air” singer is Rihanna’s most infamous ex. They went public with their relationship in 2008, and he was spotted traveling home with her to Barbados. In February 2009, Brown assaulted Rihanna following a pre-Grammy party, for which he was sentenced to five years of probation and 1,400 hours of labor. Still, they were photographed back together in December 2012 and reportedly ended their relationship again in summer 2013. “I don’t hate him. I will care about him until the day I die,” Rihanna told Vanity Fair in November 2015. (Photo: Christopher Polk/Getty Images for NARAS)

<p>Rihanna spent 2010 coupled up with the L.A. Dodgers outfielder — much to her delight. “I’m so happy. I feel really comfortable, and it’s so easy,” she <a href="http://people.com/celebrity/rihanna-relationship-with-boyfriend-matt-kemp-is-so-easy/" rel="nofollow noopener" target="_blank" data-ylk="slk:told Elle" class="link rapid-noclick-resp">told <i>Elle</i></a> that summer. But by the time she spoke with <em>Vogue</em> for the April 2011 issue, she was single. “I just kind of shut down from that,” Rihanna said. “I just let it go. I don’t ever want to have to depend on a relationship.” The star’s <a href="https://www.si.com/extra-mustard/2014/09/22/detailed-account-rihannas-dating-history-athletes" rel="nofollow noopener" target="_blank" data-ylk="slk:athlete beaus" class="link rapid-noclick-resp">athlete beaus</a> reportedly also include NBA players J.R. Smith and Rashard Lewis. (Photo: Noah Graham/NBAE via Getty Images) </p>
Matt Kemp

Rihanna spent 2010 coupled up with the L.A. Dodgers outfielder — much to her delight. “I’m so happy. I feel really comfortable, and it’s so easy,” she told Elle that summer. But by the time she spoke with Vogue for the April 2011 issue, she was single. “I just kind of shut down from that,” Rihanna said. “I just let it go. I don’t ever want to have to depend on a relationship.” The star’s athlete beaus reportedly also include NBA players J.R. Smith and Rashard Lewis. (Photo: Noah Graham/NBAE via Getty Images)

<p>Rihanna selected British boxer and model O’Shaughnessy to star in her October 2011 “We Found Love” music video, and she was <a href="http://www.dailymail.co.uk/tvshowbiz/article-2046330/Rihanna-debuts-new-boyfriend-Dudley-OShaughnessy-hand-picked-star-video.html" rel="nofollow noopener" target="_blank" data-ylk="slk:reportedly" class="link rapid-noclick-resp">reportedly</a> pretty happy about it. “Rihanna took every opportunity to get close to him and at one point she was sitting in his lap during a break from filming,” a source told the<i> Sun</i>. The two were later spotted out together at the Mahiki nightclub in London. (Photo: Ben Pruchnie/Getty Images) </p>
Dudley O’Shaughnessy

Rihanna selected British boxer and model O’Shaughnessy to star in her October 2011 “We Found Love” music video, and she was reportedly pretty happy about it. “Rihanna took every opportunity to get close to him and at one point she was sitting in his lap during a break from filming,” a source told the Sun. The two were later spotted out together at the Mahiki nightclub in London. (Photo: Ben Pruchnie/Getty Images)

<p>After Rihanna was photographed arriving at the actor’s home at midnight in March 2012, it was rumored that the two were dating. The <i>Daily Mail</i> reported that they had <a href="http://www.dailymail.co.uk/tvshowbiz/article-2119662/Rihanna-Ashton-Kutcher-enjoyed-week-fling--wants-study-Kabbalah-him.html" rel="nofollow noopener" target="_blank" data-ylk="slk:an eight-week fling" class="link rapid-noclick-resp">an eight-week fling</a> after meeting at a mutual friend’s birthday party in December 2011. (Kutcher and wife Demi Moore split in November 2011.) Not long before that, <a href="https://www.usmagazine.com/celebrity-body/news/rihanna-ryan-hotstuf-2011232/" rel="nofollow noopener" target="_blank" data-ylk="slk:Us Weekly" class="link rapid-noclick-resp"><i>Us Weekly</i></a> had Rihanna secretly dating Ryan Phillippe, but she never confirmed it. (Photo: David Livingston/Getty Images) </p>
Ashton Kutcher

After Rihanna was photographed arriving at the actor’s home at midnight in March 2012, it was rumored that the two were dating. The Daily Mail reported that they had an eight-week fling after meeting at a mutual friend’s birthday party in December 2011. (Kutcher and wife Demi Moore split in November 2011.) Not long before that, Us Weekly had Rihanna secretly dating Ryan Phillippe, but she never confirmed it. (Photo: David Livingston/Getty Images)

<p>Before the rapper <a href="https://www.yahoo.com/entertainment/kylie-jenner-reveals-stormis-last-name-not-jenner-scott-133006978.html" data-ylk="slk:welcomed a baby with Kylie Jenner;outcm:mb_qualified_link;_E:mb_qualified_link" class="link rapid-noclick-resp newsroom-embed-article">welcomed a baby with Kylie Jenner</a>, he was linked to Rihanna. They were spotted together in late 2015, but it didn’t last. (Photo: Kevin Mazur/WireImage) </p>
Travis Scott

Before the rapper welcomed a baby with Kylie Jenner, he was linked to Rihanna. They were spotted together in late 2015, but it didn’t last. (Photo: Kevin Mazur/WireImage)

<p>Both Rihanna and DiCaprio are sexy and independent, so it almost made sense that they had fallen for each other when they were spotted together several times in the past few years: at her 27th birthday bash in Paris, <a href="https://www.tmz.com/2015/01/12/leonardo-dicaprio-rhianna-partying-together-playboy-mansion/" rel="nofollow noopener" target="_blank" data-ylk="slk:at the Playboy Mansion" class="link rapid-noclick-resp">at the Playboy Mansion</a>, at Coachella in 2015, at <a href="https://www.vanityfair.com/hollywood/2016/04/leonardo-dicaprio-and-rihanna-coachella" rel="nofollow noopener" target="_blank" data-ylk="slk:Coachella in 2016" class="link rapid-noclick-resp">Coachella in 2016</a>… Still, they’ve never confirmed their romance. (Photo: Gabriel Olsen/FilmMagic) </p>
Leonardo DiCaprio

Both Rihanna and DiCaprio are sexy and independent, so it almost made sense that they had fallen for each other when they were spotted together several times in the past few years: at her 27th birthday bash in Paris, at the Playboy Mansion, at Coachella in 2015, at Coachella in 2016… Still, they’ve never confirmed their romance. (Photo: Gabriel Olsen/FilmMagic)

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