Cavallari and Dye were spotted making out in the Fulton Market area of Chicago -- a bar and restaurant district in the Windy City -- as seen in a video obtained by TMZ -- who also first identified the mystery man locking lips with Cavallari.
A source close to the former Laguna Beach star tells ET that "Kristin is having fun and is enjoying getting back into the dating scene."
"Kristin and Jay were together for a decade and broke up several months ago, so she’s not rushing anything," the source notes. "Kristin and Jeff were having a fun time, but nothing too serious right now."
Dye has been a working stand-up comedian for years, and has appeared on several MTV comedy shows, was a finalist on Last Comic Standing, and recently served as a guest panelist on Fox's The Masked Singer.
Neither Cavallari nor Dye have addressed the reports, or commented on the nature of their relationship.
"Now Kristin, I just want you to know that your name on the Zoom should be changed," Ryan Seacrest pointed out to Cavallari during an episode of On Air With Ryan Seacrest. "It says Kristin Cutler on my screen."
"Oh my God, I didn't even notice that! Wow!" Cavallari exclaimed, before sharing that she's "technically" still a Cutler. "[I'm] working on that. I'm literally going to take a note right now to change it."