For years, Rihanna has been captivating her fans over her dating life. The very talented singer’s first serious love or relationship began in 2008. It was about three years after she entered the international music industry and nobody could forget her first boyfriend who was Chris Brown. We have seen our favorite singer from finding love from a hopeless person to going on some flings and fluctuations with Drake.
However, Rihanna has been very good at keeping her personal life quite private and has kept most of her relationships under the wraps and away from media attention. Don’t Stop the Music singer, Rihanna has dated several guys over her music career and if you are her fan you might be quite interested to know all about her dating life and hooks ups.
So let’s read on further to find out who she is currently dating and who she has dated in the past throughout her musical career.
Shia Labeouf

The very handsome Honey Boy actor Shia Labeouf revealed in an interview in 2009 that he went on a date with Rihanna years back. He said, “[I was] filming a sword fight when I got the message [from Rihanna]. I said, ‘Can this be my life?’” he recalled to Playboy at the time, revealing that they decided to meet up in-person thereafter. However, the relationship did not take off beyond one date. The reason given was that the spark was not there and both of them were not quite passionate about each other. Therefore both Shia and Rihanna decided not to take things forward and be good friends.
Chris Brown
One relationship that actually grabbed the eyes of all fans was between Rihanna and Chris Brown. The singer was in a romantic relationship with Chris Brown. However, things took a ugly turn when he physically assaulted her on the night of the 2009 Grammy Awards. Chris was also order five years of probation ad was punished to stay at least 50 yards away from Rihanna. But to the fan’s surprise both of them reunited and sparked the old flame but sadly it did not last long as they parted their ways for good reasons in 2013.
Matt Kemp
Rihanna gave her love life another chance by dating Miami Marlines star Matt Kemp between January and December 2010. According to the reports from media it wasn’t much serious from any of the sides and it was all about fun and fling from both the partners. in fact, Rihanna also confirmed in one interview that she is quite happy with her new boyfriend. According to the rumors, Rihanna went back to reconciliation in 2013 that was the reason behind two partign ways but nothing was confirmed.
Ryan Phillippe
The next guy Rihanna moved upon was when she hooked up with the Shooter lead actor Ryan Phillippe. She crossed paths with Ryan at a Gucci/Roc Nation Brunch in the month of February 2010. According to the sources, they quite enjoyed their hookup life with no rules and foundations which means they totally had sex. The onlookers even claimed that the actor was also rejected when he approached Rihana at a pre Grammy event earlier that year.
Leonardo DiCaprio

One of the most famous relationships Rihanna had was with Leonardo DiCaprio. The famous Love on the Brain performer found Rihanna incredibly hot. However, both of them were not interested in looking for a relationship at that time. However, both of them reunited after a year and hung out privately at Coachella. There is no news that they were officially dating each other or not. But if we believe the rumors there was something brewing up between the duo but as things didn’t work out they parted their ways.
Karim Benzema

According to the reports, Rihanna does reportedly reachrf out to the famous soccer star during the 2014 world cup. there was a spark between the two and both of them even stepped out for breakfast dates in June 2015. Both of them were definitely dating each other, however, the relationship was not at all serious and this might be the reason after some time they took off from each other.
Lewis Hamilton
Rihanna also hooked her with the Formula One race car champion Lewis Hamilton. The Barbadian spent time with him on a private yacht in her home country. Both of them hung out together for quite a few months and also went to the Grand Kadooment Day carnival days after that.
Travis Scott

A long time before when he was with Kylie Jenner, Travis was reportedly linked to our gorgeous singer Rihanna. These rumors came out when a joint marketing collaboration with Puma was out and it was quite evident from the closeness both of them were showing that they are kinda in a relationship with each other. Many inside reports even claimed that Rihanna was quite serious about this relationship but Travis wasn’t. So just a few weeks after both of them parted ways Travis was seen hanging out with the Kardashian clan that putting a complete full stop to his budding romance with Rihanna.
Drake

Rihanna and her work collaborator the famous Drake dated on and off from 2009 that continued till 2016. According to a source, both of them have a very close connection and they will end up together not now but it could happen. Both of them were quite a popular pair but the fans never really saw a mutual attraction between them. Rihanna also denies that she has never dated Drake but has only collaborated with him on several tracks. But with the reports, pictures, and videos it’s quite tough to believe what she is saying. Now, it seems like the dust has settled on their love story book but if we hope it might be ignited again.
Hassan Jameel

Rihanna again gave her love life a chance when she started dating the Saudia Arabain businessmen in 2017. Both of them were balancing a serious relationship for about two years. Even if they had completely opposite personalities it worked out for them. The couple did not confirm their relationship publicly but the pair was spotted many times in different events and sometimes even on secret dates as well. In fact, during an interview in 2018, Rihanna even said: “I used to feel guilty about taking personal time, but I also think I never met someone who was worth it before”, making us think that Hassan was the exception. However, as their lives were too different from each other it was very hard for both of them to be together and maintain a relationship. thus, both of them mutually parted ways.
A$AP Rocky

One of the last boyfriends Rihanna was rumored to be dating was the Wild For Night rapper A$ap Rocky. Both of them were spotted many times together after her breakup with Jameel in January 2020. According to media reports, in February both Rihana and Rocky were hanging out with each other and hooking up as well. Both of them have great chemistry and by December 2020, there was news that both of them are officially a couple and celebrated Christmas together with their families in Barbados.
After reading this you may realize that your favorite singer Rihanna’s love life was quite full of hookups and breakups altogether. Now we are waiting for one final day when she decides on her lifetime partner and we really hope it’s his current boyfriend A$ap Rocky.
Do you guys think both of them will last together? or it could be someone from his exes? Share your views about it in the comments section.