Rihanna has consistently expressed her desire for companionship and a family throughout her career. In 2012, during an appearance on The Jonathan Ross Show, she remarked, “Single life is highly overrated. It’s not enjoyable.

I’ve had incredible experiences in my life, and you don’t want to go through life alone. You want to share it with someone.” Over the years, she has been romantically linked with various well-known figures, including a tumultuous relationship with singer Chris Brown and a high-profile romance with rapper Drake.

Despite her past relationships, it’s A$AP Rocky who has captured her heart. Sources close to the couple revealed to PEOPLE in January 2022 that Rocky’s overt displays of romance, such as filling rooms with flowers, have deeply impacted Rihanna. Their relationship led to the birth of their first child, son RZA, and just 15 months later, the arrival of their second child, son Riot. Rihanna’s dating history reflects her journey towards finding lasting love and fulfillment.

Chris Brown

Rihanna’s initial public relationship unfolded with singer Chris Brown. They crossed paths as teenagers early in their music careers and swiftly commenced collaborating on musical projects. Following the success of Rihanna’s “Umbrella,” Brown crafted a “Cinderella” remix, subsequently performing it alongside the singer during their joint tour in 2008.

Their romantic involvement became evident in February 2008 when they were spotted displaying affection at a Grammy Awards afterparty and during Rihanna’s 20th birthday celebration, where Brown serenaded her with “Happy Birthday.” Initially, both Brown and Rihanna asserted they were merely friends, a declaration reiterated over the subsequent months. Nonetheless, during this period, they embarked on several outings together, including attending a Kanye West concert, enjoying a summer excursion to Barbados, and indulging in a shopping spree in Sydney.

Rihanna and Brown broke up for good in April 2013.

Drake

Rihanna initially crossed paths with Canadian rapper Drake in 2005 when he appeared as an extra in her “Pon de Replay” music video. Although they initially established a friendship, their dynamic shifted to a romantic one in May 2009 when they were spotted kissing at a bowling alley in New York City. Despite this, in November of the same year, Rihanna publicly described their relationship as platonic during an interview with radio personality Angie Martinez. However, the significance of their interactions seemed to resonate more deeply with Drake, who later expressed feeling used and referenced their bowling date in his song “Fireworks.”

Despite occasional disagreements, the pair maintained a friendly rapport and collaborated on Rihanna’s 2010 track “What’s My Name.” Their joint performance of the song at the 2011 Grammy Awards further fueled speculation about the true nature of their relationship, as their onstage chemistry ignited rumors of a romantic connection.

Matt Kemp

Rihanna and Los Angeles Dodgers outfielder Matt Kemp were introduced through mutual acquaintances in November 2009. Their relationship swiftly intensified, and by January 2010, they were observed displaying affection while vacationing in Cabo San Lucas, Mexico. According to a source quoted by PEOPLE, their romantic escapade was characterized by constant displays of physical closeness, including kissing while admiring the ocean view.

Travis Scott

Rihanna and rapper Travis Scott’s romantic association began to surface towards the end of 2015, as they were seen together on various occasions. These included attending a tattoo appointment, attending a fashion week afterparty, and spending multiple evenings out in West Hollywood, California. In October, Rihanna was present at Scott’s performance at the Hollywood nightclub 1 OAK. An observer recounted to PEOPLE that after Scott’s set, the two were inseparable and openly affectionate towards each other, which was described as endearing.

ASAP Rocky

They collaborated when A$AP Rocky performed a remix of Rihanna’s track “Cockiness (Love It)” at the 2012 MTV Video Music Awards, which marked the beginning of a fruitful working relationship and a close friendship.

Their bond continued to strengthen over the years; in 2013, A$AP joined Rihanna on tour, and she made an appearance in his “Fashion Killa” music video. Their connection was further solidified in June 2018 when they were seen seated together in the front row at the Louis Vuitton Menswear show during Paris Fashion Week. Then, in December 2019, they made a joint appearance on the red carpet at the British Fashion Awards, with A$AP sporting a black suit from Rihanna’s Fenty brand, as reported by Elle magazine.

Shortly after Rihanna’s single status was confirmed in January 2020, rumors of a budding romance with A$AP emerged and were subsequently confirmed in November 2020. They spent the holidays together in Rihanna’s home country of Barbados, where sources told PEOPLE in December that they had been inseparable and deeply invested in their new relationship. A$AP openly expressed his affection for Rihanna in a May 2021 interview with GQ, referring to her as “the love of my life” and “my lady.”