Ep 20. A Date From Heck

Charles in Charge season 2 episode 20: A Date From Heck

In this episode of Charles in Charge titled "A Date From Heck," the beloved and charismatic Charles (played by Scott Baio) finds himself in the midst of yet another hilarious adventure as he navigates the unpredictable world of being a live-in nanny.

The episode begins with Charles preparing for a much-needed night off from his hectic work schedule. Excited at the prospect of a relaxing evening, he plans to go on a long-awaited date with a charming young woman named Lisa (guest star Alyssa Milano). Lisa, a co-worker of one of Charles' friends, is described as a fun-loving and outgoing person, which makes Charles even more excited about their upcoming date.

However, just as Charles is about to head out for the evening, a distraught Buddy (played by Willie Aames), one of the kids Charles looks after, bursts into the room seeking his advice. Buddy reveals that he has a secret crush on a girl in his class, but he has no idea how to approach her or ask her out. Seeing an opportunity to impart some valuable wisdom, Charles decides to postpone his date to help Buddy with his romantic predicament.

Charles takes Buddy under his wing and offers him a crash course in dating etiquette. He teaches him the importance of being confident, respectful, and genuine when talking to his crush. Buddy eagerly absorbs these lessons, but Charles soon realizes that his own date might be in jeopardy.

With Buddy's newfound confidence, he takes the plunge and asks his crush, Jane, out on a date. Much to his surprise and joy, she agrees! However, the timing couldn't be worse for Charles, as Buddy's date happens to be on the same night he had planned his romantic evening with Lisa.

Facing a dilemma, Charles must make a difficult decision: either disappoint Buddy by canceling their lessons and going on his own date, or continue helping Buddy and postpone his plans once again. Driven by a genuine concern for Buddy's well-being, Charles selflessly decides to prioritize his role as a mentor over his personal desires.

As the story unfolds, Charles finds himself in a series of comical mishaps as he sets up a whimsical movie-inspired date for Buddy and Jane. From attempting to cook a fancy dinner to creating a movie theater ambiance in the living room, Charles goes to great lengths to ensure that Buddy's date is a success.

Meanwhile, Charles' date with Lisa hangs in the balance. As the evening progresses, he tries to keep her updated on the situation to avoid any misunderstandings. Despite Lisa's initial disappointment about being stood up, Charles' honesty and dedication to his job impress her. Slowly, Lisa begins to understand the kind of person Charles truly is, further fueling her interest in him.

In the end, both dates intertwine in unexpected ways, leading to hilarious and heartwarming moments. Charles' selflessness pays off as Buddy's date turns out to be a fantastic success, while his own connection with Lisa deepens and evolves. The episode concludes with Charles realizing that sometimes, even the most well-intentioned plans can go awry, but by prioritizing the happiness and growth of those around him, he's able to find joy in unexpected places.

"A Date From Heck" is a heartwarming and entertaining episode of Charles in Charge, showcasing the endearing nature of Charles and his ability to bring people together. Whether it's mentoring a young man in matters of the heart or navigating the complexities of his own love life, Charles always manages to handle every situation with charm, humor, and a genuine desire to help others.