Top Men Rihanna Has Dated

From early industry romances to a long-term partnership and motherhood, Rihanna’s dating history spans fellow musicians, athletes, and business leaders. Below is a straightforward look at the men she’s been linked to over the years, with time frames, notable public sightings, and career intersections that fans often remember. This list focuses on widely reported relationships and high-profile linkups that drew attention at the time.

A$AP Rocky

Rihanna and A$AP Rocky were longtime friends and collaborators before their relationship became public in 2020. They attended fashion events together and appeared in each other’s projects prior to confirming their romance. The couple welcomed two sons in 2022 and 2023, stepping out for red carpets and fashion weeks as a family. They have continued to appear together at major industry events while balancing music, fashion, and business commitments.

Hassan Jameel

Rihanna dated Saudi businessman Hassan Jameel for roughly three years, with the relationship becoming public in 2017. They were photographed on vacations and at discreet outings, generally keeping a low profile. Reports indicated the relationship ended in early 2020. During this period, Rihanna focused heavily on her Fenty ventures while keeping her personal life largely private.

Drake

Rihanna and Drake had an on-and-off connection that stretched across much of the 2010s. They collaborated on chart-topping tracks and appeared together at music award shows. Public sightings and performances fueled speculation during multiple phases of their relationship. By the late 2010s, both artists had moved on, though their collaborations remain fan favorites.

Chris Brown

Rihanna and Chris Brown began dating in the late 2000s and were a highly visible couple in music and entertainment. Their relationship ended after a widely reported domestic violence incident in 2009. The two briefly reconnected in the early 2010s with a remix collaboration and appearances that suggested a short-lived reconciliation. They ultimately parted ways and pursued separate careers and personal lives.

Matt Kemp

Rihanna was linked to MLB outfielder Matt Kemp around 2010. They were photographed vacationing together and attending events during the offseason. The relationship was relatively private and reportedly ended within a year. Both continued focusing on their careers, with Rihanna ramping up music and fashion projects.

Karim Benzema

Rihanna and footballer Karim Benzema were spotted together in 2015. Their late-night outings and restaurant appearances drew international sports and entertainment coverage. Neither offered detailed public commentary, and the link faded after a brief period. Both returned to their demanding schedules in music, fashion, and professional football.

Lewis Hamilton

In 2015, Rihanna and Formula 1 star Lewis Hamilton were seen together at carnival events and parties. Photos of them traveling and attending festivities sparked dating chatter. The connection appeared casual and short-lived, with no formal confirmation from either. They moved on amicably while remaining fixtures in their respective fields.

Travis Scott

Rihanna and Travis Scott were linked in 2015 amid music collaborations and appearances at fashion and industry events. Reports suggested a brief, private relationship during a busy period for both artists. The link ended quietly as each pursued separate projects. Both later moved into other high-profile relationships and continued releasing music and launching brand ventures.

Shia LaBeouf

Rihanna and Shia LaBeouf were connected after a reported date in the late 2000s. Shia later indicated it did not develop into a relationship. At the time, both were early in major career moments across music and film. The brief link remains a footnote in both stars’ histories.

Josh Hartnett

Rihanna and Josh Hartnett were rumored to be dating in the late 2000s after being seen together at industry events. Coverage focused on a handful of outings and mutual friends within entertainment circles. Neither offered extensive details, and the connection seemed to fade quickly. Both continued to work steadily in music, film, and television.

Ryan Phillippe

Reports in the early 2010s linked Rihanna and Ryan Phillippe after they were seen at the same parties. The speculation centered on a few overlapping appearances during a busy awards season. No official confirmation followed, and the rumor faded. Each continued with separate projects and public commitments.

Leonardo DiCaprio

Rihanna and Leonardo DiCaprio sparked headlines after being photographed at parties and events in the mid-2010s. The coverage focused on social settings and mutual friends rather than a defined relationship timeline. Neither publicly confirmed anything beyond casual interactions. The link remained speculative and brief.

Dudley O’Shaughnessy

Model Dudley O’Shaughnessy worked with Rihanna on a high-profile music video and was later seen with her socially. Their connection centered on the project’s promotion and a cluster of appearances afterward. Reports suggested a short-lived link that did not evolve into a longer relationship. Both returned to their respective careers in modeling and music.

J. R. Smith

Rihanna and NBA player J. R. Smith were the subject of rumors in the early 2010s after nightlife sightings in New York. The coverage relied on club appearances and social media chatter. No formal relationship was confirmed, and the speculation soon tapered off. Smith remained in the NBA spotlight while Rihanna expanded her business ventures.

Share the names you think should be added to this list in the comments.