From Drake To Asap Rocky: Rihanna's Romantic Relationships Are Always Trending

Since Rihanna debuted on the music scene in the early 2000s, the world has been curious about her personal life. The Anti singer, 32, has been romantically linked to a number of high-profile men, and fans are likely familiar with Drake and Hassan Jameel, to name a few. But we’re sure you’ve forgotten about a couple of celebrities Rihanna has been associated with in the past! Continue reading to learn more.

1. One of the most renowned couples of the late 1990s was Rihanna and Chris Brown. The two hitmakers, who rose to prominence in the 2000s with chart-topping singles like “Pon de Replay” and “Run It,” were both adolescents at the time. Throughout their difficult relationship, they had their ups and downs.

2. Before they started dating, Rihanna and Drake were friends and partners. They met in 2005 while she was filming a music video in Toronto, but their first date was not until 2019. They collaborated on a number of songs throughout the years, including “Work,” “Take Care,” and “What’s My Name,” and were said to have had an on-again, off-again romance until 2016.

3. Rihanna and her pal A$AP Rocky, 31, became romantically connected in early 2020 after being seen hanging out only days after her breakup with Hassan. The twosome kept the romance alive throughout the year, especially after being seen getting very intimate on a dinner date just days after Thanksgiving in November.