Who's the Boss? Season 2 Episode 5
Who's the Boss?
Season 2

Ep 5. Tony the Matchmaker

  • TVG
  • October 29, 1985
  • 6.9  (89)

Tony the Matchmaker:

In the second season of the beloved sitcom "Who's the Boss?", episode 5 brings us an entertaining and heartwarming story titled "Tony the Matchmaker." Filled with laughter, unexpected twists, and heartwarming moments, this episode captures the essence of this charming series.

The episode begins with Tony Micelli, a former professional baseball player turned housekeeper, navigating the challenges of single parenthood for his daughter, Samantha. His life takes an unexpected turn when Angela Bower, a successful advertising executive and single mother to Jonathan, hires him as her live-in housekeeper.

In "Tony the Matchmaker," Tony finds himself reluctantly thrust into the role of a cupid when his good friend, Max Muldoon, decides to move to California to pursue his acting career. Max is a very attractive man who believes he was meant to be a movie star. However, he seems to lack the same luck in love that he hopes to find in Hollywood.

Seeing an opportunity to help his friend find love, Tony takes it upon himself to become Max's matchmaker. With his charismatic personality and genuine desire to help, Tony starts by arranging a series of blind dates for Max. Wanting to make sure these potential matches are perfect for Max, Tony goes the extra mile in his matchmaking endeavors.

As Tony goes about finding eligible women for Max, the audience is treated to a series of hilarious moments as Tony's unique choices for dates don't always result in perfect pairings. From accidental mix-ups to humorous misunderstandings, Tony's efforts to find true love for Max are filled with comedic mishaps.

Meanwhile, tensions rise between Angela and her mother, Mona, who is visiting the Bower household. Though they love each other deeply, their different personalities often clash. Mona is a carefree and spontaneous woman, while Angela is more structured and focused on her career. As the episode progresses, we witness Angela and Mona's conversations, filled with witty banter and occasional disagreements, as they both strive to understand and appreciate their differing perspectives.

Back in the world of matchmaking, Tony's efforts seem to be leading nowhere, and Max becomes increasingly discouraged. However, in a surprising turn of events, Tony's dedication and determination eventually pay off when he manages to organize a chance encounter between Max and an intriguing woman named Samantha.

Samantha, a bright and independent woman, unexpectedly enters Max's life, and they hit it off right away. As their connection grows deeper, the audience witnesses a heartwarming bond form between these two characters. Max, initially skeptical of Tony's matchmaking abilities, begins to realize that true love can be found in the most unexpected places.

With Angela and Mona also growing closer throughout the episode, "Tony the Matchmaker" paints a picture of the importance of relationships and the value of family. As the characters navigate love, friendship, and understanding, the episode delivers an important message about finding happiness, even in the face of adversity.

Filled with funny moments, heartfelt conversations, and surprising twists, "Tony the Matchmaker" showcases the endearing and relatable characters that have made "Who's the Boss?" such a beloved sitcom. As the episode comes to a close, audiences are left with a renewed appreciation for the importance of love, laughter, and the bonds that make a family. So, sit back, relax, and enjoy this delightful episode that encapsulates the magic of "Who's the Boss?"

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Who's the Boss?, Season 2 Episode 5, is available to watch and stream on Sony. You can also buy, rent Who's the Boss? on demand at Hulu online.
  • First Aired
    October 29, 1985
  • Content Rating
    TVG
  • Language
    English
  • IMDB Rating
    6.9  (89)
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