On Saturday, the models were spotted at the Malibu Chili Cook-Off, joined by his sister Bella and a few other friends. The group hit up the carnival attractions and cheered on pal Jesse Jo Stark’s performance at the event. The following night, they stopped by Nobu for dinner.
A source tells PEOPLE that Jenner had a “fun weekend in Malibu.”
“Kendall seems great,” the source says. “She’s spending time with Anwar. She obviously likes him, but both nights they were with a group of friends. She wasn’t affectionate with Anwar.”
The outing comes after Jenner, 22, and Anwar, 19, were caught making out at a CFDA Awards afterparty in New York City in June — around the same time she struck up a romance with Philadelphia 76ers player Ben Simmons.
At the time, a source told PEOPLE that Anwar’s sisters Gigi, 23, and Bella, 21, likely didn’t mind their brother getting flirty with their friend.
“Gigi and Bella wouldn’t be bothered by it,” said the insider. “Anwar is a total ladies man, so it does seem random that he and Kendall would hook up, but also expected.”
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Following the kiss with Anwar, Jenner’s relationship with Simmons, 22, began picking up steam, and the pair even vacationed in Mexico with Jenner’s sister Khloé Kardashian and her boyfriend Tristan Thompson in August. Nevertheless, a source previously told PEOPLE that the model remains “very protective” over her relationship with Simmons — and her dating life in general. (She has yet to publicly address their relationship.)
Simmons is currently in Philadelphia and hasn’t been spotted with the model in over a week.