The History of Rihanna’s relationships, from Drake to A$AP Rocky

A$AP Rocky is the man who Rihanna has finally discovered and who makes her feel like the only girl in the world. The couple, who reportedly had love and children on the mind, announced their first child’s impending arrival in January 2022.

However, before dating the rapper, the Savage X Fenty designer tried her luck at finding love with a number of men who turned out to be unsuitable.

Here is a timeline of all Rihanna’s relationships:

Chris Brown

When they were both too young and upcoming musicians in 2005, Chris Brown and Rihanna met. But their relationship didn’t begin until 2007.

When it was discovered that Brown had physically assaulted Rihanna on their way home from a pre-Grammy party, the couple had a sensational breakup in February 2009. The “Look at Me Now” singer entered a plea of guilty of felony assault, was sentenced to probation, community service, and counselling for domestic abuse, all of which were completed in March 2015.

Early in 2013, Brown and Rihanna had a brief reconciliation. At the time, the “Love the Way You Lie” singer told Rolling Stone, “I realized it was more essential for me to be happy. Even if I made a mistake, it was my fault. However, they had permanently broken up by April of that year.

Matt Kemp

After her initial breakup with Brown, Rihanna started dating MLB player Matt Kemp. After being seen together on New Year’s Eve in 2009 and subsequently on a vacation to Mexico in the beginning of 2010, the couple ignited dating rumors.

The ex-LA Dodgers outfielder exclaimed to US Weekly in May 2010: “Yeah! I love that chick! She is just a good time. I adore being in her presence”

However, due to the “Bitch Better Have My Money” singer’s demanding schedule, they parted up by December 2010.

Karim Benzema

Then, the relationship between Rihanna and soccer player Karim Benzem was brought up. She apparently met the Real Madrid star at a nightclub, and in June 2015, the two were seen together in a New York restaurant.

In 2017, the pair officially called it quits. A source close to Benzema revealed the separation to the Spanish magazine Don Balon Rosa, saying, “Rihanna liked Karim, and she had a lot of fun with him”. She said that she will always love Chris Brown but assured him that she did not wish to hurt his feelings. It was difficult to compete, according to Rihanna.

Lewis Hamilton

Because the “Where Have You Been” singer was seen vacationing with Formula 1 driver Lewis Hamilton in her home Barbados in August 2015, it appears that Benzema and Rihanna were not an exclusive couple. They were seen together in a New York city nightclub, but their relationship quickly fell apart.

Travis Scott

A month later, Rihanna was photographed getting close to Travis Scott, another well-known figure. In September 2015, she was making out with the rapper during a New York Fashion Week event.

They kept their relationship a secret, but later that year, when Scott was interviewed for his Complex cover story and questioned about the “Umbrella” singer, he instructed the journalist to “do (me) like that, man”. He then responded, “Creative”, “Inspiring”, and “Muse”, when asked to sum her up in three terms.

Leonardo DiCaprio

Page Six stated that Leonardo Dicaprio and Rihanna had seen kissing in a Paris nightclub in January 2016, despite claims from Insiders close to the pair that they were “Just Friends”.

When the A-listers were spotted hanging out together at Coachella that April, romance suspicions about them intensified even more.


Also in 2016, when they appeared at one other’s concerts, Rihanna and Drake created their own romance rumors.

In a heartfelt acceptance speech for Rihanna’s Video Vanguard award at the MTV Video Music Awards that August, the “Hotline Bling” rapper officially declared his love for her, saying, “Someone I’ve been in love with since I was 22”.

A few months later, Rihanna and Drake had broken up due to scheduling conflicts, but they were still close friends and ‘still in each other’s lives”.

But by June 2018, Rihanna had admitted to Vogue that she and Drake were “not friends anymore” but also “not enemies either”.

Hassan Jameel

While on vacation in Spain in June 2017, Rihanna was seen making out with Saudi businessman Hassan Jameel. This is a genuine relationship. Rihanna has admitted to loving him to friends, and she certainly appears infatuated. They have been spending a lot of time alone together and seem quite serious. They seem to be having a great time together.

When Jameel was spotted out to dinner with Rihanna and her mother, things seemed to have taken a serious turn. The majority of their relationship was kept out of the public eye.

After over three years together, the pair decided to end their relationship in January 2020.

A$AP Rocky

Nearly immediately after her split from Jameel, Rihanna started seeing A$AP Rocky, although at the time, a source told The Sun that the billionaire was “reluctant to put a label on it as it’s so soon after Hassan”.

Prior to going public in November 2020, the couple looked to get closer by spending a lot of time together in New York City.

Rocky himself finally discussed his connection with Rihanna in May 2021, telling GQ that she was the “love of his life” and “the one”.

In January 2022, the couple made Rihanna’s pregnancy public with a snowy picture session in the rapper’s neighbourhood of Harlem.

The Fenty Beauty founder gave birth to their son four months later.

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