The Larry Sanders Show (1992)

S3E11 Larry Loses a Friend

Title: Larry's Friendship Tested Plot: Jon Lovitz enthusiastically pursues a hesitant Darlene, trying to win her over despite her reservations. As he attempts to charm her, Larry finds himself caught in the middle, grappling with the impact this pursuit has on their friendship. Tensions rise as Darlene weighs her feelings, leading to unexpected consequences for all involved.