Season
Episode
- Episode 1: It Happened One Summer (1)
- Episode 2: It Happened One Summer (2)
- Episode 3: Ad Man Micelli
- Episode 4: The Heiress
- Episode 5: Tony the Matchmaker
- Episode 6: Custody (1)
- Episode 7: Custody (2)
- Episode 8: Hunk of the Month
- Episode 9: Thanksgiving at Mrs. Rossini's
- Episode 10: The Prodigal Father-in-Law
- Episode 11: The Graduate
- Episode 12: Tony the Nanny
- Episode 13: Junior Executive
- Episode 14: Educating Tony
- Episode 15: Gotta Dance
- Episode 16: The Babysitter
- Episode 17: Jonathan Plays Cupid
- Episode 18: When Worlds Collide
- Episode 19: Losers and Other Strangers
- Episode 20: Tony for President
- Episode 21: Not with My Client, You Don't
- Episode 22: Angela's New Best Friend
- Episode 23: There's No Business Like Shoe Business
- Episode 24: The Unnatural
- Episode 25: The Anniversary Show
- Episode 26: Charmed Lives
Who's the Boss? Season 2 Jonathan Plays Cupid
A former professional baseball player, along with his preteen daughter, moves into New York advertising executive Angela Bower's house to be both a housekeeper and a father figure to her young son. Tony 's laid-back personality contrasts with Angela's type-A behavior.
