It's Garry Shandling's Show (1986)

S1E15 Dinner with Garry

Garry arranges a dinner for his mother, hoping to spark a connection with her physician. As the evening unfolds, tensions rise and unexpected chemistry develops, leading to surprising revelations. Garry navigates the complexities of his mother’s emotions while trying to ensure that the night goes smoothly. As they share laughter and stories, both his mother and the doctor confront their feelings, creating a memorable evening that may change their lives forever.