The world’s richest female singer Rihanna is pregnant with her first child with male singer A$ap Rocky after two years of dating. Before deciding to “choose the right person” for her current rapper boyfriend, singer Diamond was involved with many famous people.

1. Hassan Jameel

Rihanna and Saudi Arabian businessman Hassan Jameel began dating in 2017. In an interview with Vogue magazine in 2019, Rihanna shared: “I’m dating. I’m actually in a relationship.” We’ve been in a serious relationship for a while now, everything is going very well and I feel extremely happy.”

Rihanna and Hassan Jameel – Saudi Arabian businessmen

However, the couple decided to “go their separate ways” in January 2020 because there were so many differences in life that the two could not find common ground.

2. Drake

Rihanna and the famous Canadian male rapper had a complicated friendship-love relationship from 2009 to 2017.

The two had their first date when Rihanna broke up with her ex-boyfriend, singer Chris Brown, in 2009. It wasn’t until 2014 that paparazzi captured images of the female singer holding hands with Drake in London. Two years later, the two had a bold collaboration in the MV “Work”, and their romantic actions while performing on stage raised dating suspicions. At that time, Drake and Rihanna were the hottest suspected couple in the entertainment industry and fans were looking forward to making their relationship public.

Drake and Rihanna at the 2016 VMAs

The relationship between the two ended when the female tycoon confirmed to Vogue magazine: “Currently we are no longer friends, and there is no enmity between us, it’s as simple as that.”

3. Travis Scott

The boyfriend of Hollywood’s number one IT girl Kylie Jenner had a passionate time with the owner of the Fenty brand when the two were together at New York Fashion Week in 2015. According to E! Online: “Travis and Rihanna are officially dating. The two of them are very serious. Travis really likes Rihanna.”

However, the talented couple also broke up some time later.

4. Matt Kemp

Rihanna and basketball player Matt Kemp confirmed they were dating in January 2010, one year after she broke up with Chris Brown.

After a year together, Matt said goodbye due to Rihanna’s busy work schedule.

Matt Kemp and Rihanna were still passionate

US Weekly said: “Matt can’t keep up with Rihanna’s tour schedule. He was tired of escorting the singer to performances all over the world and wanted a more normal relationship.”

5. Chris Brown

Rihanna and Chris Brown dated from 2007 to 2009. They quickly became the most powerful young couple in the music industry at that time.

The young couple broke up when Rihanna accused Chris of abusing her. The incident shocked showbiz when images of the female singer’s bruised and bloody face spread across newspapers and social networks.

Rihanna’s disfigured face

After breaking up, the couple reunited in 2013 for a short period of time but still did not get good results.

The “many talented” singer has always affirmed his love for Rihanna for many years even though the two are no longer together and Chris shared all about his breakup with Rihanna in the documentary. “Chris Brown : Welcome to My Life” in 2017.