Meanwhile, the core couples continue to evolve. Jules and Grayson (Josh Hopkins) are now comfortably married, bickering lovingly about everything from towels to aging. Their relationship provides the season’s emotional anchor, especially as they navigate the trials of raising the ever-adorable and sarcastic toddler Stan. Bobby (Brian Van Holt), Jules’s lovably dim ex-husband, has fully become the gang’s eccentric, barefoot philosopher—now a professional golfer living on a boat, naturally.
Season 5 also introduces a few new recurring characters, including Grayson’s quirky, competitive son, Tom (Bob Clendenin), who gets more screen time as the group’s resident weirdo. The show also doubles down on its guest stars, with recognizable faces like (the late, great) James Michael Tyler popping up. Cougar Town - Season 5
The season’s plotlines are classic Cougar Town : Ellie attempts to prove she has a soul; Andy (Ian Gomez) chases a bizarre dream of becoming a stand-up comedian; and the whole gang gets obsessed with a high-stakes game of “Penny Can” that somehow becomes a metaphor for their friendships. There’s also a hilarious multi-episode arc involving a mysterious “cul-de-sac crew” rival group, complete with their own handshake and cooler wine glasses. Meanwhile, the core couples continue to evolve