Rihanna’s Wild Dating History

Rihanna’s Dating History: A Glimpse into the Pop Icon’s Romantic Life

Rihanna, one of the most influential figures in music and fashion, has long kept her personal life under wraps—yet, her romantic relationships have been a topic of intense media scrutiny over the years. The singer, known for her bold persona and empowering music, has been involved in several high-profile relationships, each one making headlines for different reasons. Her early romances were characterized by both public passion and personal drama, with one relationship in particular making headlines worldwide.

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This highly publicized pairing was followed by a brief, yet significant relationship with someone in the sports world, which, although less tumultuous, still garnered attention. The pairing was short-lived, but it marked a shift toward her trying to maintain a sense of normalcy in the spotlight. As time went on, the singer found herself entangled with another famous artist, sparking rumors of a deeper connection. Their collaboration in both music and public appearances made fans believe there was something more than just friendship. Despite the undeniable chemistry, this relationship also proved to be short-lived, with both individuals parting ways after several years of speculation. Following a more private and low-key relationship with a businessman, the singer seemed to have found lasting love again, this time with another musician. Their relationship, however, wasn’t just about the two of them—it was a public celebration of both love and family as they welcomed their first child together, marking a new chapter in her life. Check our Rihanna’s full Dating History Below RELATED: A$AP Rocky Rejects Plea Deal In Gun Assault Case, Could Face 24 Years

1. Chris Brown

• Instagram: @chrisbrownofficial
• Dating Period: 2007 – 2009 (with a brief rekindling in 2012)
• Details: Rihanna and Chris Brown had a highly publicized and turbulent relationship. They broke up after the infamous incident in 2009 when Chris was charged with assaulting Rihanna. They la

2. Drake

• Instagram: @champagnepapi
• Dating Period: 2009 – 2016 (on and off)
• Details: Rihanna and Drake have had an on-again, off-again romance over the years, with much speculation about their relationship status. They’ve been spotted together multiple times, and their romantic history includes collaborating on tracks like “What’s My Name?” and “Take Care.” However, the relationship never seemed to fully stick.

3. Matt Kemp

• Instagram: @mattkemp
• Dating Period: 2009 – 2010
• Details: Rihanna dated the MLB player Matt Kemp after her breakup with Chris Brown. The relationship seemed more low-key, but they split after about a year

4. Jameel Jefri

• Instagram: Not active on Instagram (He’s a Saudi billionaire businessman).
• Dating Period: 2017 – 2020
• Details: Rihanna was linked to Hassan Jameel, a billionaire heir to the Saudi Arabian conglomerate Abdul Latif Jameel. They were seen in public multiple times, though they mostly kept the relationship private. They reportedly broke up in early 2020.

5. A$AP Rocky

(2020–Present)

• When: Rihanna and A$AP Rocky started dating in 2020, and by 2022, they confirmed they were expecting their first child. They’ve been very public since then, especially about their growing family.
• Instagram:
  • Rihanna: @badgalriri
  • A$AP Rocky: @asaprocky

6. Ryan Phillippe (2011, rumored)

 

• When: Rumors circulated in 2011 that Rihanna and actor Ryan Phillippe were dating, though neither of them ever confirmed the relationship.
• Instagram:
  • Rihanna: @badgalriri
  • Ryan Phillippe: @ryanphillippe

7. Travis Scott (2015, rumored)

 

• When: In 2015, there were rumors about Rihanna and rapper Travis Scott being involved. They were spotted together a few times, but neither confirmed anything serious.
• Instagram:
  • Rihanna: @badgalriri
  • Travis Scott: @travisscott

8. Leonardo DiCaprio (2015, rumored)

 

• When: There were rumors in 2015 about Rihanna and Leonardo DiCaprio being romantically linked after they were spotted together at several events. They never publicly confirmed a relationship.
• Instagram:
  • Rihanna: @badgalriri
  • Leonardo DiCaprio: (No Instagram, but you can find him on other social media outlets.)

9. Karim Benzema (2015, rumored)

 

• When: There were some rumors in 2015 that Rihanna and French soccer star Karim Benzema were seeing each other, though neither confirmed the romance.
• Instagram:
  • Rihanna: @badgalriri
  • Karim Benzema: @karimbenzema

 

10. Brock O'Hurn (2017, rumored)

 

• When: Rihanna was rumored to have had a fling with actor Brock O’Hurn, though this was never confirmed.
• Instagram:
  • Rihanna: @badgalriri
  • Brock O’Hurn: @brockohurn