Yes, Dear (2000)

S3E6 Mr. Big Shot

As Greg and Kim organize a family getaway to Lake Tahoe with the Hughes, Greg recalls a fancy establishment known as The Pinnacle Room that his affluent uncle often praised. Viewing dining there as a symbol of success, he’s disheartened when Kim informs him they can't secure two rooms at the lodge due to Jimmy and Christine's budget constraints. During the trip, Jimmy grows frustrated upon discovering Greg booked a larger room for himself. Confronted by Jimmy, Greg reveals he intentionally chose the bigger space, feeling constrained by Jimmy's financial situation. However, after a disastrous dinner at the pretentious Pinnacle Room, where nothing goes right, Greg realizes that Jimmy's modest lifestyle has its own merits.