Rihanna Dating History: Her Former Partners, Ranked By Net Worth

Key Takeaways

Rihanna’s dating history includes several high-profile men, such as Drake, Chris Brown, Matt Kemp, and Hassan Jameel, whose net worth of $1.9 billion surpasses Rihanna’s fortune.
ASAP Rocky and Rihanna began their relationship in early 2021 and have since welcomed two children, with their second born in 2023.
When they first got together, ASAP Rocky had a net worth of $10 million, but his relationship with Rihanna appears to have inspired greater ambition in his business and creative pursuits.

From the moment Rihanna burst onto the scene, she became a global sensation, dominating the music charts and the business world. Rihanna’s net worth is currently estimated at $1.4 billion, fueled by her chart-topping hits and groundbreaking business pursuits. Her chart-topping hits are not the only thing keeping the rumor mill churning – her romantic escapades have also sparked endless fascination.

The singer has never been shy about her desire for love and companionship. As she candidly shared on The Jonathan Ross Show in 2012, “Single life is so overrated. It sucks. I have such incredible experiences in my life. You don’t want to live your life and then meet someone. You want to share your life with someone.”

Rihanna clearly enjoys the finer things in life, and her exes, many of whom are also celebrities, have bank accounts to match. Over the years, Rihanna has been linked to several high-profile men, including a tumultuous chapter with Chris Brown and a much-talked-about romance with rapper Drake. Let’s explore Rihanna’s dating history, the men she has shared her life with, and their net worth.

6 ASAP Rocky

ASAP Rocky’s Net Worth (Estimated): $25 Million

Rihanna and A$AP Rocky first met in early 2012 while rehearsing for the MTV VMAs. Though they had chemistry, both were with other people at the time. Fast-forward to 2020, Rihanna had ended her relationship with billionaire Hassan Jameel, while A$AP Rocky had split from model Jasmine Daniels the previous year. The two artists confirmed their relationship in 2021 and are now doting parents to two sons, RZA and Riot.

When their romance began, A$AP Rocky was already a self-made millionaire with a net worth of $10 million. However, their relationship seems to have spurred even greater ambition in the rapper and entrepreneur. Rocky has expanded his portfolio with strategic investments, becoming an equity holder in the Swedish fintech company Klarna and taking on a leadership role with Mercer + Prince, a Canadian whiskey brand.

His creativity also extends to his position as a creative director for Formula 1 partnerships. The Grammy-nominated hip-hop artist has also been prolific in his music career, having released four studio albums, 42 singles (including 25 as a featured artist), eight promotional singles, and 31 music videos. As of 2024, A$AP Rocky’s net worth has skyrocketed to an estimated $25 million.

ASAP Rocky’s Net Worth
$25,000,000

Current Relationship Status
Dating

Relationship Span
2020 – Present

Rihanna And ASAP’s Net Worth Compared
Rihanna is $1.375 Billion richer than ASAP Rocky

5 Chris Brown

Chris Brown’s Net Worth (Estimated): $50 Million

Chris Brown and Rihanna first crossed paths as teenagers in 2005, when both were newcomers in the music industry with debut albums that heralded their rise to stardom. Their connection evolved over time, with their romantic relationship officially beginning in 2007, making Brown Rihanna’s first public partner. In 2009, just before a scheduled Grammy Awards performance, their relationship took a tragic turn when Brown violently assaulted Rihanna.

Brown pleaded guilty to felony assault and was sentenced to community labor, probation, domestic violence counseling, and a restraining order. Despite the traumatic incident, Rihanna surprised many in 2013 when she confirmed to Rolling Stone that she and Brown had reconciled, reigniting a relationship that had remained the subject of relentless speculation. The rekindling was short-lived, as Brown revealed in May 2013 that they had ended things again.

Today, Chris Brown’s net worth is estimated at $50 million, with his fortune stemming primarily from music. Rising to prominence with his multi-platinum debut album at just 16, Brown has since sold over 140 million records worldwide, making him one of the world’s best-selling music artists. Notably, Brown is one of the highest-grossing African American touring artists of all time. In 2019, Billboard ranked him as the third most successful R&B and hip-hop artist of the 2010s, following Drake and Rihanna.

Chris Brown’s Net Worth
$50,000,000

Current Relationship Status
Single

Relationship Span
2007 – 2013

Rihanna And Brown’s Net Worth Compared
Rihanna is $1.350 Billion richer than Chris Brown

4 Matt Kemp

Matt Kemp’s Net Worth (Estimated): $75 Million

After her tumultuous relationship with Chris Brown and a brief fling with Drake, Rihanna found herself in the spotlight again, this time linked to professional baseball player Matt Kemp. The pair met through mutual friends in November 2009, and sparks flew quickly. By January 2010, they were seen vacationing together in Mexico, confirming their budding romance.

Although their time together was drama-free, the romance fizzled out after 11 months, reportedly due to Kemp’s struggle to keep up with Rihanna’s demanding schedule and constant traveling. Matt Kemp’s baseball career began in 2003 with the Los Angeles Dodgers, where he established himself as a star athlete. Over the years, he played for multiple MLB teams, including the San Diego Padres, Atlanta Braves, and Cincinnati Reds.

During his career, Kemp picked up lucrative deals that made headlines, most notably an eight-year contract with the Dodgers worth $160 million. Since retiring from professional baseball, Kemp has transitioned into a mentoring role, assisting MLB players with training and serving as an advisor for his former team, the Dodgers. As of 2024, Matt Kemp’s net worth is valued at $75 million, stemming from his MLB contracts, endorsement deals, and post-retirement businesses.

Matt Kemp’s Net Worth
$75,000,000

Current Relationship Status
Single

Relationship Span
2009 – 2010

Rihanna And Kemp’s Net Worth Compared
Rihanna is $1.325 Billion richer than Matt Kemp

3 Travis Scott

Travis Scott’s Net Worth (Estimated): $80 Million

In 2015, rumors swirled around Rihanna and Travis Scott, leaving fans and media outlets buzzing with questions about their relationship status. The duo initially tried to keep their romance under wraps, but entertainment outlets were quick to uncover the truth. E! News was the first to confirm their relationship, with TMZ following up by providing further evidence. While the media clamored for details, Rihanna and Scott decided to keep their relationship out of the public eye.

Reports suggested that the Sicko Mode rapper was uncomfortable with the intense public scrutiny, even becoming frustrated when their relationship details were leaked. Speculation also arose that Rihanna felt embarrassed about their pairing, which may have fueled their cautious approach. By 2016, the pair had quietly parted ways after roughly a year together. While the exact reason for their breakup remains unclear, some sources suggest that personality differences between the two played a role.

Travis Scott has skyrocketed to the top of the rap industry. The 10-time Grammy nominee has sold over 8 million albums worldwide, earning millions through music, endorsements, and tours. He also founded the Cactus Jack record label, signing rising stars like Sheck Wes, Don Toliver, and SoFaygo. Scott was one of the highest-paid artists at his peak. He reportedly earns $40–$60 million in a touring year. As of 2024, Travis Scott’s net worth is estimated at $80 million.

Travis Scott’s Net Worth
$75,000,000

Current Relationship Status
Single

Relationship Span
2015 – 2016

Rihanna And Scott’s Net Worth Compared
Rihanna is $1.320 Billion richer than Travis Scott

2 Drake

Drake Net Worth’s (Estimated): $250 Million

Rihanna and Drake’s on-again, off-again relationship could easily provide material for a compelling romance drama. Their first encounter dates back to 2005 when Drake appeared as an extra in Rihanna’s Pon de Replay music video. The pair remained friends for years, but things turned romantic in May 2009 after they were spotted sharing a kiss at a New York City bowling alley. Rihanna denied they were anything more than friends, and shortly after, she began dating baseball star Matt Kemp.

Drake later expressed his frustration, admitting he felt used and referred to himself as “a pawn” in her life. Even with the emotional tension, the pair maintained a professional relationship, collaborating on multiple hit tracks. After her brief relationship with Travis Scott, Rihanna and Drake rekindled their romance, which led to a buzzworthy moment during the 2016 MTV Video Music Awards. During his speech at the event, Drake professed his love for Rihanna, admitting he had admired her since he was 22.

However, Rihanna, fresh off the media frenzy surrounding her past relationship, was reportedly uncomfortable with the public declaration. Although the pair got matching shark tattoos later that year, by 2018, their relationship had officially ended. Reflecting on their dynamic, Rihanna admitted in an interview, “We don’t have a friendship now, but we’re not enemies either.” By 2021, Rihanna had covered up her shark tattoo with a crown.

Today, Drake has a net worth of $250 million. He has built his fortune through various ventures, including his record label, a successful liquor brand, and lucrative endorsement deals with major companies like Nike. The five-time Grammy winner has had a highly successful music career and co-founded OVO Clothing, OVO Sound, and DreamCrew Entertainment. As one of the best-selling artists worldwide, with over 170 million units sold, Drake is the highest-certified digital singles artist in the United States.

Drake Net Worth
$250,000,000

Current Relationship Status
Single

Relationship Span
2009 – 2016

Rihanna And Drake’s Net Worth Compared
Rihanna is $1.150 Billion richer than Drake

1 Hassan Jameel

Hassan Jameel’s Net Worth (Estimated): $1.9 Billion

Rihanna threw everyone for a loop when she stepped out with Saudi businessman Hassan Jameel in 2017. The pair kept their relationship private, leaving the media in the dark until they were spotted celebrating New Year’s Eve together in London. The pair continued to keep things private until April 2017, when they were spotted together in Tokyo, which all but confirmed their relationship. Over the next three years, they were occasionally photographed at events and vacations.

The couple parted ways in early 2020, reportedly due to differing lifestyles and compatibility issues. Hassan Jameel might not be as famous as some of Rihanna’s other exes, but he is undoubtedly the richest. The billionaire businessman is the deputy president and vice chairman of Abdul Latif Jameel Company, a family-owned conglomerate with exclusive rights to distribute Toyota vehicles in Saudi Arabia and several other countries.

The company also has diversified interests in multiple sectors, like mobility, energy, water, finance, health, and investments, with operations in 35 countries and over 11,000 employees. In 2024, Forbes named the Jameel family the top Arab family business. Thanks to his leadership and the family’s extensive business empire, Hassan Jameel’s net worth is estimated at $1.9 billion, making him the only one among Rihanna’s ex-partners to surpass her net worth.

Hassan Jameel’s Net Worth
$1,900,000,000

Current Relationship Status
Single

Relationship Span
2017 – 2020

Rihanna And Jameel’s Net Worth Compared
Hassan Jameel is $500 Million richer than Rihanna