The 18-year-old "Keeping Up With the Kardashians" star is said to be infatuated with the "Loyal" singer after she has partied with him on several occasions since his release from jail in June.
Kendall reportedly went back to Chris' place after the MTV Video Music Awards held on Aug. 24 at The Forum in Inglewood, Calif. and "hung out with friends until 5 a.m.," Us Weekly's Wednesday print edition reported, according to Enstarz.
"She's obsessed with Chris," a source told the celebrity magazine. But Kris Jenner, Kendall's mom, is reportedly not happy that her model daughter is "into bad boys."
Kendall was seen cozying up to Rihanna's former boyfriend in a series of Instagram photos from a party in July. The above photo was one of the photos taken at the said bash.
Kendall was also spotted partying with Chris before the infamous nightclub shooting in West Hollywood in August that left Suge Knight injured, Hollywood Life reported.
Meanwhile, just this August, Chris and Tran made headlines after one of the singer's Instagram posts sparked speculation that the two are settling down and having a child together, The Mirror reported.
On Aug. 21, the "Don't Think They Know" crooner took to the image-sharing site and revealed that he and Tran were celebrating their five year anniversary.
Brown posted a photograph of her lover and wrote, "damn near 5 years and this woman still putting up with my s-t."
"Need to have this baby and stop playing! Lol! My WCW," he added, referencing the social media acronym for Woman Crush Wednesday.
The couple started dating in the wake of Brown's breakup from Rihanna, who he was convicted of assaulting in 2009, according to Cover Media.
New reports are claiming that the Grammy-winning recording artist is now determined not to mess things up again with Tran.
"He knows what Karrueche wants, he's not stupid," an insider told Hollywood Life. "He really doesn't want to make a commitment and then somehow mess it up and break her heart."