Rihanna's controversial relationship with Chris Brown can be considered one of the most challenging chapters of RiRi's life. It was in 2008 when the two became an item. Dating rumors came after the Caribbean Queen and CB collaborated for a remix version of the former's hit song, "Umbrella," in 2007. Chris Brown even joined some of Rihanna's concert tours to perform the duet. Although the female singer was mired in dating controversy with Josh Hartnett during that time, fans could not help but notice RiRi's chemistry with the rapper, who was quick to clarify that he is "just friends" with the co-singer.

How did they become official?

Rihanna and Chris Brown made their relationship official at the birthday party of the "Diamonds" singer where the rapper ended his performance with a kiss for the celebrant. The couple was also seen getting cozy at a Jamaican hot pool shortly after making their romance public. The Barbados Babe was the first to speak up about her relationship with the rapper, stating that they started out as friends before they developed a close bond.

Since then, the two have made no effort to hide their relationship from the public. In fact, RiRi brought Chris Brown to her hometown, where they spent their summer vacation. The "We Found Love" artist even introduced her beau to her family in Barbados during their visit.

What went wrong?

According to Hollywood Life, things started to fall apart after Chris Brown allegedly assaulted his girlfriend in the midst of an intense argument. Rihanna even sustained black eyes and busted lips after she was beaten up by her partner. The "Look At Me Now" artist immediately turned himself in after the physical assault was made public.

After the case was closed, Chris Brown dedicated a video apology to Rihanna, which turned out to be a PR stunt (Sorry, not sorry!). Following their whirlwind legal battle, the ex-lovers collaborated for RiRi's "Birthday Cake" and CB's "Turn Up The Music" in 2011 and 2012, respectively.

Although she knew how the public would react to her reunion with Chris Brown, Rihanna said she will continue to care for her ex-beau despite the unfortunate turn of events in their relationship.

"I don't hate him. We're not friends, but it's not like we're enemies," the female artist previously said.

Similarly, a source close to her said RiRi has been thinking about the possibilities if she ended up marrying the "Zero" rapper. "Rihanna can't help thinking "what if?" and how different her life would be if she and Chris tied the knot," they said.

It was also revealed that the "Pon De Replay" artist struggled to move on from her relationship with CB despite the fact that their romance ended on a bad note. The affiliate, however, clarified that Rihanna is no longer in love with the rapper.