The Complex Dating History Of Rihanna Explained

With the world possibly ending soon (via Euractiv), we'd really like it if Rihanna could take over. In approximately four years, the singer turned entrepreneur launched a cosmetic company, a lingerie line, and a high-end fashion accessories house, making her the richest female musician on the planet (via Forbes). Ironically, it wasn't from her music (we will wait for as long as it takes for a new album) but her other ventures, each of which set new standards in inclusivity. Either way, we're glad she got the running-the-world memo.

And while the "not all men" crowd may disagree, a woman doesn't need a man to wear a crown, especially if the woman is Rihanna. The singer famously told an interviewer in 2014, "I'm not looking for a man, let's start there," when asked about what she's looking for in a man (via YouTube). The musician doesn't need to either, they gravitate towards her, as we all do. From the terrible (Chris Brown) to the not-terrible-at-all (ASAP Rocky), read more about the people Rihanna's dated below.

ASAP Rocky called Rihanna 'The One'

On June 23, 2021, Rihanna and ASAP Rocky were both spotted together at New York's Barcade on a date that night, making it an auspicious day for everyone except the bouncer who did not know who they were (via Revolt TV). If the bouncer had read ASAP Rocky's feature on GQ, he would've known Rocky had declared Rihanna, "The love of my life" just a month before. When asked what it's like to be in a relationship, he said, "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."

Bumble probably saw a spike in downloads after that article came out. The two have been dating since November 2020 after staying friends for man years (via People). But before the picture-perfect relationship with Rocky, Rihanna was in a few other long-term relationships. One of them was with Hasan Jameel.

Hassan Jameel and Rihanna dated for three years

Hassan Jameel has many credentials. According to Elle, is a Saudi businessman whose family owns Abdul Latin Jameel, an organization that owns rights to sell Toyota Motor vehicles in Saudi Arabia. He is a billionaire and he is also Rihanna's ex. Jameel was first seen with Rihanna in June 2017, when they were photographed kissing in Spain (via People). A source told Us Magazine, "Rihanna and Hassan understand each other very well and their personalities mesh well together ... They're both so different, but it works for them."

In a profile with Interview Magazine, Rihanna admitted that she was, "of course," in love with Jameel but when interviewer Sarah Paulson asked if she's planning to get married, Rihanna said, "Only god knows that, girl. We plan and god laughs, right?"

Jameel and Rihanna dated for three years before breaking it off in the beginning of 2020 because "their lives were too different and it was hard to maintain a relationship," according to a People source.

Drake and Rihanna had an on-and-off relationship for years

Before Jameel, "God's Plan" put Rihanna in the path of someone who probably lived a similar lifestyle. Drake and Bad Gal RiRi topped Billboard charts with their song "What's My Name" in October 2010 and gave a very public display of affection at the 2011 Grammy Awards (via Billboard). This was in the midst of the two denying rumors of them dating, which had sparked in 2009 after they were photographed "making out all night," according to a Page Six source.

"She's the ultimate fantasy," he told Rolling Stone. "I mean, I think about it. Like, 'Man, that would be good.' We have fun together, she's cool and shit. But we're just friends. That's my dog for life." However, Drake soon professed his love on stage at the 2016 MTV-VMA Awards, "We love the woman who hasn't changed since day one. She's someone. .. she's someone I've been in love with since I was 22 years old, she's one of my best friends in the world," and the two kissed right after (via YouTube). The on-and-off relationship continued with many subsequent collaborations like "Take Care" and "Work" but ended in 2016.

She dated Chris Brown

Rihanna was rumored to have dated a few other people like Leonardo DiCaprio and Shia LaBeouf (via Us Magazine). But one of her first long-term relationships was with singer  Chris Brown. The two met as teenagers in 2005 but began dating in 2008, per Hollywood Life. The relationship only lasted for a year.

On the day of the 2009 Grammy Awards, Brown physically assaulted Rihanna in a car, leaving her with multiple bruises and black eyes. He was arrested and sentenced to five years of probation and domestic violence counseling but Brown never took responsibility for his gruesome actions. In a documentary about his side of the story, Brown actively justified his violence as reactions to Rihanna's actions (via Grazia). One reviewer on IMDb aptly called it "Abuse and Excuses."

In a candid interview with Vanity Fair, Rihanna opened up about her frame of mind when she got out of the relationship, saying, "You want the best for them, but if you remind them of their failures, or if you remind them of bad moments in their life, or even if you say I'm willing to put up with something, they think less of you — because they know you don't deserve what they're going to give."

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.