Charlie appears to be under the impression that the romantic connection he shares with The Waitress is typical and appropriate for a romantic partnership to develop. When he tells Ruby Taft that he was only using her to make The Waitress jealous, he says that “a quality woman doesn’t do that; she doesn’t say ‘yes’ right away; she says ‘no’ to a man, for years, like ten years.” He makes this statement after noting that she banged him “almost instantly.” (“Charlie and Dee Find Love”). On the other hand, the Waitress could hardly be considered a “quality woman” in this context because she banged Dennis so rapidly. More explanation is available about Charlie Dy on our site.
After what Dee refers to as 15 years, Charlie eventually gets some attention from the Waitress after he convinces her that he’s the person she could have the baby she’s always wanted with, and the two sleep together. Charlie’s plan works, and the Waitress pays attention to Charlie. Soon after that, Charlie changes his heart and decides to leave the Waitress at his apartment when she begins to express concerns about the living circumstances she and the baby are subjected to. She says it is one thing to trap someone with a baby, and it is another thing to become trapped by the baby. After receiving several phone messages from the Waitress, he ultimately concludes that he should ignore her. (“Dennis’ Double Life”)
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Charlie likely gave up his virginity to Stacy Corvelli when they were in high school together. After a few years, she reappears in his life and manipulates him into believing that he is the biological father of her boy, Tommy. Tommy is the son of another student who attended the same secondary school, Jimmy Doyle. (“Charlie Wants an Abortion”). In a sequence cut from the Season 5 DVD, it is hinted that Stacy is the only woman he has ever had sexual relations with up until that point and that the experience may have been traumatic for him.
Charlie was the only member of The Gang up until the eighth season who had not engaged in sexual activity during the period covered by the series. This “record” was broken due to his relationship with Ruby Taft. (“Charlie and Dee Find Love”).
Related to serials
When Dee reprimands Charlie in season 3 for being sexually aroused by Dennis’ drawings of women in skimpy dresses while they are both working in a sweatshop under Paddy’s, Charlie makes his first public display of his sexual interest in Dee. (“The Aluminum Monster vs. Fatty Magoo”) In an earlier episode, while the two were being held captive by the McPoyles, they shared their first kiss. However, Charlie immediately slapped her in the face after the kiss. (“The Gang Gets Held Hostage”) In the tenth season, Charlie and Dee have sexual encounters alone, and the other characters are absent. (The Gang Misses the Boat) According to the writer Megan Ganz, it is later disclosed in season 14 that he was also raped by Dee on a different occasion, despite her belief that the encounter was consenting. This information comes to light even though she thought the encounter was consensual. (It’s Time to Put an End to This Gang)During Charlie’s ski trip, he has a one-night stand with a so-called model from Bulgaria named Tatiana. It is subsequently revealed that Tatiana was a prostitute Frank had hired. (“The Gang Hits the Slopes”)