The Kardashians star and "La Jumpa" rapper were seen leaving Dave Chappelle's comedy show together at Delilah in West Hollywood on Aug. 1.
For the occasion, Kendall, 27, wore a black off-the-shoulder sheer top paired with a black lace bra. As for Bad Bunny, the 29-year-old wore a dark brown leather jacket, sporting a black T-shirt underneath.
The pair's late-night outing comes just days after the two stepped out for a dinner date at Sushi Park in West Hollywood. The model and musician proved they were also on a roll with their July 26 outing, color-coordinating in all-black attire.
Kendall and Bad Bunny first sparked romance rumors back in February after they were spotted out on a double date with Justin and Hailey Bieber. Since then, the two have embarked on numerous outings including after-parties, courtside games and more.
However, neither Kendall nor Bad Bunny have publicly commented on the status of their relationship. And they may not anytime soon, considering the Grammy winner likes to keep details of his personal life close to his chest.
"I know [people are] going to say something," he told Rolling Stone in June. "People know everything about me, so what's left for me to protect? My private life."