The final-season episode featuring Tom Skilling as Mr. Dearborn’s dining companion is “Caramel,” episode 7 of The Bear’s fifth season.
In the episode, the restaurant is enduring a difficult service while trying to accommodate every reservation. Mr. Dearborn arrives with Chicago weatherman Tom Skilling, whose presence adds a distinctly local detail to the episode. Neil Fak keeps the pair entertained with personal stories while the kitchen improvises around a failing stove.
The title “Caramel” also connects to the episode’s dessert sequence. Marcus and Luca serve Marcus’s father a dessert involving raspberries and caramel sauce hidden inside a candle, giving the frantic service an unexpectedly tender emotional payoff.
Viewers may confuse the answer with “Raspberries,” because raspberries appear prominently in the same late-season storyline. “Caramel,” however, is the episode title attached to the dining-room visit by Skilling and Dearborn. It is the seventh of eight standard episodes released on June 25, 2026.