Whether it's street style and high fashion moments, the lucrative lane she's carved through her multiple businesses, or the question of "where's the album sis?", multi-hyphenate Rihanna's every move is a new headline. The latest subject on all of our radars is our favorite bad gyal's love life. Though currently wrapped up in a whirlwind romance with long-time friend A$AP Rocky, who the singer has dated has always been of public interest and public opinion (if you know, you know).
Though she has been in her fair share of high-profile romances throughout the year, Rihanna has always maintained a sort of elusive quality to her. Even more so in recent years as she has navigated single life and a previous relationship with a particular billionaire. Something that has us thinking the good sis can be tamed is rapper boyfriend A$AP who took to GQ recently to reveal our girl Riri is "the One" and the love of his life. His words.
However, Rihanna was recently spotted commenting the sentence "If I was a paragraph" underneath a photo explaining that if you aren't happy single, you aren't going to be happy taken. While it could mean trouble in lovers and friends paradise, a little birdie mentioning she covered her matching tattoo with former beau Drake amid her new romance with A$AP could signify she might be feeling something similar (i.e. Mr. Rocky could be "the one").
Either way, we thought there's no time like the present to explore the past. Let's review Rihanna's relationship history by taking a walk down memory lane: Exes Edition.
Chris Brown
Chris Brown and Rihanna attend the 55th Annual GRAMMY Awards at STAPLES Center on February 10, 2013 in Los Angeles, California.
Christopher Polk/Getty Images for NARAS
From 2007 to 2009, Rihanna dated singer Chris Brown. The relationship ended in turmoil in 2009 due to a devastating domestic violence incident resulting in Brown being charged with making criminal threats and assault. The two would eventually rekindle their relationship briefly between 2012 and 2013, even briefly collaborating on songs again together, the raunchy "Birthday Cake" and the middle finger to the court of public opinion "Nobody's Business".
In 2015, Rihanna would reveal to Vanity Fair about her seemingly toxic bond with her ex and what ultimately led her to leave.
"I was very protective of him. I felt that people didn't understand him. But you know, you realize after a while that in that situation you're the enemy. 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."
Drake
Rihanna (L) and Drake pose onstage during the 2016 MTV Video Music Awards at Madison Square Garden on August 28, 2016 in New York City.
Kevin Mazur/WireImage
Another on-again off-again relationship in Riri's life, Drake and her reportedly began their first of a couple of flings in May 2009, after meeting in 2005. In an April 2012 to Max Choice FM, the Toronto rapper shared about their romance:
"I think that we have a connection that's established for life and that is that I love her and support her unconditionally, and I like to think that she feels the same way. Do I fancy her? Of course, I mean who wouldn't? Look at her, she's stunning. Of course I do. Yeah, no, she's incredible. But you know, it's one of those things that it's a maybe one day, maybe not."
As the pair dwindled and rekindled throughout the years, the Grammy winners have gifted fans with plenty of dope tracks, including "What's My Name?", "Too Good", "Take Care", and "Work". In reference to those glorious collabs, Drake told Zane Lowe:
"We do well together as a team. I think we do great music together. It's tough to do guy-girl collabs. I think [the chemistry] is what makes the records better, though. It's something genuine there. We're not forcing some story on people. A lot of the music that we make and the energy that we bring is genuine. We have a lot of genuine energy between us."
In 2016, sparks ignited again between the two before parting ways months later. In 2018, Drake unfollowed Rihanna after she revealed to Vogue:
"We don't have a friendship now, but we're not enemies either. It is what it is."
Matt Kemp
Rihanna dated professional baseball player Matt Kemp from January to December 2010. Allegedly, Kemp initiated the split because of the songstress' hectic schedule. Back when the two were an item, Rihanna giddily opened up to ELLE, calling their relationship her "peace":
"I have a boyfriend. I'm so happy. I feel really comfortable, and it's so easy. 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."
Travis Scott
Singer Rihanna and Travis Scott are seen coming out of Coppelia restaurant in Soho on August 12, 2015 in New York City.
Raymond Hall/GC Images
Like her alleged flings with actors Leonardo Dicaprio and Ryan Phillippe, this short-lived romance with rapper Travis Scott has only been confirmed by sources close to the two. However, those of us who spotted the subtle hints towards each other between Riri and Trav during their time together, we know the things! We peeped!
Hassan Jameel
Rihanna seen at 1-Oak nightclub after partying with rumor boyfriend Hassan Jameel after attending the 2018 Grammy Awards after party on January 28, 2018 in New York City.
Robert Kamau/GC Images
Perhaps her most private relationship was the one she started in 2017 with billionaire beau Hassan Jameel. In fact, though revealing in a cover story with Interview magazine that she was "of course" in love with him, she was pretty quiet publicly about their time together.
"I'm actually in an exclusive relationship for quite some time, and it's going really well, so I'm happy."
The couple reportedly split in January 2020.
A$AP Rocky
Rihanna and ASAP Rocky arrive at The Fashion Awards 2019 held at Royal Albert Hall on December 02, 2019 in London, England.
Jeff Spicer/BFC/Getty Images
We'll call this chapter "Lovers & Friends" as A$AP Rocky and Rihanna have friendship as a foundation. Before taking their relationship to the next level by becoming an item, the two artists were friends. Riri starred in A$AP's "Fashion Killa" music video in 2013 and the rest is history. Seeing them paint the town red on date nights galore has been an energy we live for!
While it's been speculated the pair have dabbled into "more than friends" territory throughout the years, nothing has served as confirmation as much as the photos of them together in the last year. And in 2021, A$AP took things a step further publicly by confirming their relationship to GQ.
"She amounts to probably, like, a million of the other ones... I think when you know, you know. She's The One."
Featured image by Kevin Mazur/Getty Images for Savage X Fenty Show Vol. 2 Presented by Amazon Prime Video
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Skylar sees things differently. At the time, she was shooting content on her iPhone. Temi came into the picture with a new perspective, an understanding of tech, and, eventually, a camera. “He doesn't give himself enough credit,” Skylar says. “He wasn't just my tripod. He wasn't just standing behind the camera and going ‘click.’ He was giving advice. He was giving me insight to how I could look at things from a different perspective. And I was like, 'Oh, he’s an artist.' I think it was maybe a heartbeat of that kind of energy of like, ‘Baby, can you take this picture?’ And it turned so quickly into, we're partners. We can work together in a way where we're advancing each other's creative thinking.”
The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Temi and SkylarCj Hart @hartbreakToday, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak