In particular, Charlie kelly demonstrates this trait when he seduces and manipulates a beautiful and wealthy girl by the name of Ruby and then insults, rejects, and humiliates her in front of a packed mansion of guests, all for the simple reason that the Waitress finally acknowledged his existence in her life. He does this to humiliate her in front of everyone there. When he was given authority in the bar by Frank in the episode “Mac Bangs Dennis’s Mom,” he also orchestrated intricate schemes. In this episode, he successfully convinces Dennis to humiliate himself and get into a fight with Mac sexually. He also persuaded Dee to give him favors and assistance in seducing the waitress. His infatuation with the Waitress fuels Charlie’s surprising capacity for cruelty and manipulation. More explanation is available on Charlie Dy.
The other members of the Gang coined the term “Charlie Work” to refer to the less desirable tasks that needed to be completed around the bar. Charlie is the only member of the Gang who demonstrates an honest work ethic, as he is the only one prepared to take on these tasks. Charlie is the only character in “Charlie Work” who demonstrates a genuine interest in successfully clearing the bar’s routine health code inspection. In the episodes where he and the Gang get jobs outside the bar, he tends to have the most hustle. In fact, in the episode “Sweet Dee Has a Heart Attack,” in which he and Mac and Dennis are working in a mail room, he is the one who discovers a significant mail system conspiracy. In one of the scenes, he discusses how he received mail from a fictional character named Pepe Silvia, who eventually evolved into an internet meme.
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Charlie’s dating life doesn’t go very well, but he has a secret crush on the Waitress, a recurrent supporting character on the show. She doesn’t feel the same way about him. Even though she has repeatedly stated that she will never be interested in him, he makes a concerted effort to gain her favor by going to great lengths. The waitress always finds herself in a worse situation due to Charlie’s advances toward her because his behavior has led to her being fired from her employment and having sexual encounters with Frank and Dennis. Despite this, he appears to have had success with other women, such as in the pilot episode
Serials and datings
“The Gang Gets Racist,” in which he starts dating a girl he met at a community center, only to have her dumped when he tries to use her to get a date with the Waitress. Despite this, he appears to have had luck with other women. Another instance of Charlie having a steady girlfriend is seen in the episode “Charlie and Dee Find Love,” in which he starts dating wealthy heiress Ruby Taft (Alexandra Daddario), who genuinely appreciates him for who he is. Charlie and Dee Find Love can be found on Netflix. Sadly, Charlie destroys this relationship by admitting that he is only interested in her to get closer to the waitress. In the episode “The Gang Misses the Boat,” Charlie and Sweet Dee have a passionate night together following an intense session of slam poetry that they both participated in together. However, the next day, they declined to discuss anything that had happened the night before. Other occurrences throughout the series lend credence to the idea that these two characters may harbor some emotions for one another. However, in the episode “Time’s Up for the Gang,” it is revealed that Dee raped Charlie after he realized he didn’t want to have sex with her, but she held him pinned down and covered his mouth until she was finished.