Rihanna’s relationships: A timeline from Chris Brown to ASAP Rocky

Rihanna. Pic Credit:

Rihanna’s love life has been fascinating to her fans ever since she hit the music scene.

Let’s take a look back at all of her known relationships and how they turned out.

Chris Brown

Chris Bown
Chris Brown. Pic Credit:

The singer’s first serious relationship began in 2008 when she began dating Chris Brown. Prior to the start of their relationship, the pair were seen crossing paths at events, including the Z-100 Jingle Ball held in Madison Square Garden in 2005.

Brown also collaborated with Rihanna on a remix of her hit song, Umbrella. He titled the track Cinderella and even took to the stage with her in Asia to perform it live.  

Brown sang for Rihanna at her 21st birthday and reportedly ended the song with a kiss. The couple was also spotted flying off to Barbados and spending lots of time together.

Things took a turn in 2009 when Brown was accused of beating Rihanna the night before the Grammys. Photos emerged showing Rihanna in a hospital with a bruised face.

Brown was arrested and charged with battery. He was sentenced to five years of probation, community service, and counseling.

To the surprise of her fans, Rihanna forgave Brown and they rekindled their relationship in 2012. She told Oprah Winfrey on an episode of Oprah’s SuperSoul Conversations that Brown was her “true love.”

The pair were seen sitting together at basketball games and going on vacations. However, they split for good in 2013.


Drake holding two awards at the 2019 Billboard Music Awards.
Drake at the 2019 Billboard Music Awards. Pic Credit:

Shortly after Brown and Rihanna split in 2009, Rihanna was spotted on a supposed date with Drake in New York City.

A source told Page Six that the pair were at Lucky Strikes Lanes & Lounge “making out all night.” However, Rihanna denied that the two were dating during an interview on Angie Martinez’s radio show.

Rumors began to swirl once again in 2010 when the two collaborated on the single, What’s My Name?

In 2013, Drake told Ellen DeGeneres that he and Rihanna had their moment and that he’ll always support her.

It seemed as though they had more moments together, as they were spotted by paparazzi holding hands in London in March 2014. However, Rihanna continued to deny claims that the two were ever together.

They continued to put out good music together, though. The pair’s hit single, Work, stayed on the top of the charts for weeks.

In 2016, Drake publicly professed his love for Rihanna as he presented her with the Michael Jackson Video Vanguard Award. He said, “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. All my adult life, I’ve looked up to her even though she’s younger than me. She’s a living breathing legend in our industry.”

Rihanna, however, was taken aback by Drake’s compliments.

In 2018, she told Vogue: “Waiting through that speech was probably the most uncomfortable part. I don’t like too many compliments; I don’t like to be put on blast. She also said of her relationship with the rapper: “We don’t have a friendship now, but we’re not enemies either. It is what it is.”

Hassan Jameel

Rihanna found love again with billionaire businessman Hassan Jameel. In December 2016, Rihanna was photographed holding hands with Jameel.

In 2017, the pair were also seen vacationing together in Ibiza and Spain. The vacations didn’t end there, though. In January 2018, the two were spotted on a balcony in Paris and later in the year, in Mexico.

The two continued to be spotted on outings until Us Weekly broke the news of their breakup in January 2020.

ASAP Rocky

Rihanna and ASAP Rocky posing together.
Rihanna and ASAP Rocky. Pic Credit:

Rihanna quickly moved on and was reportedly “hanging out and hooking up,” with ASAP Rocky in February 2020, according to a source.

By December of that year, the couple was official, as they were spotted on a yacht during the holidays.

In May 2021, ASAP Rocky referred to Rihanna as the “love of [his] life” in an interview with GQ.

The couple is now expecting a child together, as revealed during a stroll in New York over the weekend.

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