The two, along with Bella Hadid, were spotted out with friends in Malibu, California, on Friday.
Kendall and the 19-year-old model, along with his sister, Bella Hadid, and a group of friends, hit up the Malibu Chili Cook-Off in Malibu, California, on Friday. Kendall and Anwar, who were caught making out in June, were all smiles as they were spotted cozying up and going down a carnival slide together.
Kendall, 22, looked casual in a white tank top with blue jeans, black combat boots and a green baseball cap. Anwar opted for a grungier look, wearing black jeans and a black band tee. The group of friends also enjoyed Jesse Jo Stark's performance at the event, with Kendall and Bella taking to their Instagram Stories to share brief moments from their night out.
A couple months ago Kendall and Anwar were spotted locking lips at a CFDA Awards after-party in New York City. The steamy smooch came less than a week after rumors started swirling that Kendall and NBA star struck up a romance, however, a source told ET that the reality star and Anwar were "nothing serious."
"Anwar and Kendall are just having fun for now," the source said at the time. "Both of them recently got out of relationships, and don't want anything too serious."
"Kendall is best friends with Anwar's sisters, Gigi and Bella, and she respects them tremendously," the source continued. "Kendall would never want to do anything to put her relationship with Anwar's sisters in jeopardy. Kendall and Anwar have known each other for years and have always been flirtatious and this is just another sign of that. The two enjoy one another's company and things could change, but for now, it's nothing serious."
Meanwhile, following their fun at the fair, the group then headed over for dinner at Taverna Tony at the nearby Malibu Country Mart. An eyewitness tells ET that Bella and Kendall arrived at the restaurant at around 8:30 p.m. with about four guys -- though it was clearly just a friendly outing. Bella's boyfriend, The Weeknd, wasn't there.
"There wasn't any PDA," the eyewitness says, adding that while Kendall cuddled up to one guy in particular, it didn't look romantic. According to the eyewitness, the Keeping Up With the Kardashians star and Bella were recognized by other diners as soon as they walked in, but didn't necessarily try to avoid attention.
The group was spotted chatting it up over a bottle of wine and glancing at their phones in between conversations, before sharing a sweet moment with fans. "Two girls approached them, and Kendall and Bella took selfies with them on their phones," the eyewitness says. One of the guys then picked up the bill, and the group left around 9:30 p.m.
Kendall's outing comes weeks after she and Simmons enjoyed a vacation in Mexico with Kendall's sister, Khloe, and Tristan Thompson.
See more on the twosome in the video below.