Rihanna's Revenge: Inside Her Storied Romantic History

After having her trust shattered by Chris Brown, the pop star has opted to put herself first and only let a handful of guys get close

By Natalie Finn Jun 29, 2017 12:00 PMTags
Rihanna Jon Kopaloff/FilmMagic

Consider Rihanna the phoenix risen from the dating ashes.

Barely 21 when her seemingly idyllic relationship with 19-year-old sweetheart Chris Brown turned violently ugly, the Good Girl Gone Bad artist could have been forever sucked into that circle of drama.

She was sucked in, for awhile, requesting that the judge not issue a 100-yard restraining order after Brown pleaded guilty to assaulting her, and choosing to reconcile with him on and off for the next four years. She even sat with Brown's mother at one of his probation hearings in 2013. To be sure, her ongoing relationship with Brown won her plenty of critics, as there are always countless people who confidently know exactly what they would do in a similar situation ready to weigh in with their opinions.

So Rihanna was in for it from both sides—those who were outraged on her behalf and simultaneously disturbed by her choices.

But if you look more closely at Rihanna's choices, particularly the ones she's made since fully cutting ties with her first love, they appear to be the choices of a young woman who's determined to not let just any man hold sway over her ever again. Not that that's stopped the guys from veritably lining up to take their chances with the perennially unattainable artist.

Rihanna's Top 12 Instagrams

"While we're on the topic of Instagram, I just wanna say it's a bit of an awkward vibe tonight. I gotta say, I've never been in the same room as so many guys who have DM'd my ex girl," Drake, who has publicly pledged allegiance to RiRi over the years, joked during his monologue while hosting the 2017 NBA Awards this week. "There's a lot of DPs sent to that inbox, man, y'all are some dogs."

Yet for all of the visibly good times captured in photos taken all over the world, on stage, on yachts, at clubs and concerts, sporting events and parties, and, most recently, in swimming pools, Rihanna has refrained from being tied down. She's the Lady Leo, and yet she's not even as into settling down (albeit temporarily) as her dear friend Leonardo DiCaprio is—nor is she necessarily interested in casual hookups.

"When you love somebody, that's different," she explained to Vanity Fair in 2015, surprising those who assumed that singing authoritatively about sex meant Rihanna was acting out her (or their) fantasies on a daily basis. "Even if you don't love them per se, when you care enough about somebody and you know that they care about you, then you know they don't disrespect you. And it's about my own respect for myself. A hundred percent."

Andreas Rentz/Getty Images

In her own way, she has revolutionized the art of dating while female—people are as interested in her love life as ever (and Drake makes up for anyone who isn't) but no one really bats an eye when she changes beaus as some would when, say...Taylor Swift would step out with a new guy and be instantly scrutinized for rushing into the next thing.

Rihanna, in all her swaggy glory, has her timing down to a leisurely science that suits her. Her established badassery and relentless sex appeal and the fact that she's usually surrounded by admirers make it seem as though there would be more guys linked to her, but really—by young Hollywood standards—not all that many have been granted access into her orbit. And most of them have just been near enough to catch a few rays from her glow...

Shia LaBeouf

The rumors were out there, but the Transformers star played coy with GQ in 2008. "My friends were like, 'Are you serious, bro? Are you f--king kidding me? Why didn't you tell me about that?' I was like, 'I really don't know her like that,'" he told the magazine. "or weeks they were singing that 'Umbrella' song everywhere I walked. And those are my people!"

Finally LaBeouf admitted to Playboy in 2009, "It never got beyond one date" in 2007. "The spark wasn't there. We weren't passionate about each other in that way, so we remain friends."

But they'll always have Disturbia and "Disturbia."

Chris Brown

By all accounts, they met as teenagers in 2005 and by 2006 were hanging out at events like the Nickelodeon Kids' Choice Awards. But even though they were seemingly attached at the hip, they kept insisting on their respective free agency, with Rihanna telling MTV News in 2008, "We are best friends, honestly, like brother and sister."

Just a few months later, Brown said in a radio interview, "Our relationship is growing. We started off as friends and we're getting a little bit closer now." It wasn't long before they assumed the throne as the prince and princess of pop-R&B, a power couple in the making.

The events of Feb. 8, 2009, are well-documented (as well as still speculated about), but they resulted in leaked police photos of Rihanna's bruised face shocking the world and Brown pleading guilty on June 23, 2009, to felony assault. He was sentenced to five years of probation and six months of community labor—a sentence that would set off a years-long legal odyssey for Brown that saw him being alternately praised for good behavior and punished for various other infractions. 

"He was definitely my first big love," Rihanna told Diane Sawyer in November 2009, her first time speaking publicly about what happened. "The more in love we became, the more dangerous we became for each other."

That was hardly the end for them, as a 50-yard restraining order (Rihanna wanted it quashed entirely, but the judge insisted on at least 50 yards, 10 at industry events) didn't keep the two apart for the long haul. They would reunite off and on, including in 2012 when Brown guested on a remix Rihanna's racy track "Birthday Cake" and she joined him for "Turn Up the Music."

Confirming that they were dating once again, Rihanna told Rolling Stone at the beginning of 2013, "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. After being tormented for so many years, being angry and dark, I'd rather just live my truth and take the backlash. I can handle it." 

Acknowledging their history, she added, "He doesn't have the luxury of f--king up again. That's just not an option. I can't say that nothing else will ever go wrong. But I'm pretty solid in the knowing that he's disgusted by that. And I wouldn't have gone this far if I ever thought that was a possibility. He made a mistake, and he's paid his dues. He's paid so much. And I know that's not a place he would ever want to go back to. And sometimes people need support and encouragement, instead of ridicule and criticism and bashing."

Though they would continue to hang out together amid breakup rumors, they seemingly split up for good in April 2013.


Meanwhile, Rihanna met this guy in 2009 and, though they certainly liked each other, the timing couldn't have been more wrong.

"I definitely was attracted to Drake, but I think it is what it is, like, it was what it was," Rihanna told Hot 97's Angie Martinez in November 2009. "We didn't want to take it any further. It was at a really fragile time in my life, so I just didn't want to get too serious with anything or anyone at that time." Drake further complicated their status, or lack thereof, saying, "People thought I was dating Rihanna, and that was semi-true."

If this were a romantic comedy, Rihanna would have realized that the answer has been staring her in the face (and gushing about her, ranting about her, fighting for her honor, declaring his love for her, distancing himself from her, and back again) for the past eight years, but...

It's only real life, and they remain cordoned off in the friend-collaborator-and-tour-mate zone.

Matt Kemp

Rihanna met the baseball player, then an up-and-coming star with the L.A. Dodgers, in late 2009 and they dated for the better part of a year. She called it "nothing too serious" in April 2010, but just a few months later...

"I'm so happy. I feel really comfortable, and it's so easy," RiRi gushed in Elle's July 2010 issue about being with Kemp. She added, "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."

Alas, not long after she told Marie Claire UK, "I feel like I smile for real this time," their on-the-go schedules did them in. 

No hard feelings, though, as Kemp called Rihanna "a good friend" and told Us Weekly in 2011, "We've all got busy lives and we're working on our careers and concentrating on our careers. Like I said, I wish her all the best of luck and she wishes me all the best of luck."

In hindsight, however, the paparazzi wouldn't let them be and all the attention they attracted took its toll. "It's pretty much overwhelming," Kemp admitted in a 2012 interview on In Depth With Graham Bensinger. "It's not something I've ever been used to. I'm not used to going to a grocery story or to just somewhere simple and people following you around." He recalled his grandma seeing a picture online of him and his ex hugging and telling him "'you can't be doing that.'"

Apparently he handled the scrutiny like a champ, however, because Rihanna told Vanity Fair in 2015, "We were just three months in and I liked his vibe, he was a good guy, and then paparazzi got us on vacation in Mexico. He handled it well; I didn't. I got so uncomfortable because now what? He's not even able to be seen with [another] girl, because I'm dragged back into headlines that say he's cheating on me, and I don't even [seriously] know this guy. Some guys [I'm linked to]...I don't even have their number. You would not even believe it."

Leonardo DiCaprio

These kindred spirits have had some hot 'n' heavy moments but are at the end of the day just enjoying the truly tremendous lives they've carved out for themselves. Sometimes together if they happen to be in the same time zone.

Karim Benzema

Rihanna bonded with the pro soccer player (whom she had tweeted at in late 2014) over his tireless work ethic—something she surely appreciated and identified with—as summer 2015 got underway.

Lewis Hamilton

Later in the summer of 2015, however, the avid sports fan was keeping company with Formula 1 driver Hamilton, but all he would say was, "You know, I've known Ri for a long time. We've been friends for a while. We get to hang out every now and again."

Ultimately, with both Hamilton and Benzema in the picture, Rihanna just wasn't ready to "put a label on anyone," a source told E! News. "She is not at any point in her life now ready to settle just for anyone, but she is enjoying the time she has with her friends and also focusing on work."

Travis Scott

"Creative," "inspiring" and "muse" were the three words the "Antidote" rapper offered to describe her in an interview for the December 2015/January 2016 issue of Complex, before which he reportedly kept the interviewer waiting because he was off somewhere with Rihanna.

A source told E! News in September 2015 that Scott was "very into her," but...well, that was his misfortune.

Hassan Jameel

After devoting herself to "Work," and a rekindling-reminiscent episode with Drake in mid-2016, Rihanna was just spotted kissing the Saudi businessman. Jameel is deputy president and vice chairman of his family's $1.5 billion company, Abdul Latif Jameel, which has held Toyota distribution rights in Saudi Arabia for half a century. We also know what a Euro-football fan Rihanna is, and he happens to own a professional soccer league—the Jameel League, naturally.

The duo, both 29, were surreptitiously snapped making out in a swimming pool amid what theoretically should have been private surroundings in Spain, thereby forcing their blossoming relationship further into the spotlight than either might have been ready for. 

Such is what Rihanna was forced to get used to at a very early age, even before her initial relationship with Chris Brown spiraled out of control.

"Sometimes it's the first time I'm meeting this person [any person]—and then all of a sudden I'm 'with them.' It freaks me out," she admitted to Vanity Fair. "This industry creates stories and environments that can make you uncomfortable even being friends with someone. If you see me sitting next to someone, or standing next to someone, what, I'm not allowed to do that? I'm like, are you serious? Do you think it's going to stop me from having a friend?"

Moreover, her fame has had to make her much more cautious about whom she lets get close to her. No wonder she's stuck close to just a few people and was willing to play the rebound game—she at least knew them.

"I'm the worst. I see a rumor and I'm not calling [them] back," she said. "I've had to be so conscious about people—what they say and why people want to be with me, why people want to sleep with me….It makes me very guarded and protective. I learned the hard way."