In the concluding episode of the 12th season, Charlie succeeds in persuading the Waitress to have sexual relations with him by pointing out that they might be able to have a child together, which she has always desired. (“Dennis’ Double Life”)In the first episode of season 13, it is strongly implied that Charlie took part in a three-way orgy with Mac, Frank, and a sex doll designed to look like Dennis while Dee witnessed them all get off while she was naked. (“The Gang Helps Paddy’s Become Great Once More”)
In Season 14, Frank and Charlie have overnight guests, two European backpackers who take the position of Alexi and Nikki, who were their Airbnb renters in Austria. More explanation is available on Charlie Dy.
Janelle Jenkins — He dated Janelle to demonstrate to The Waitress that he was not a sexist and that Janelle was genuinely interested in him. He used the fact that she liked him to his advantage. (“The Gang Gets Racist”).
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The Waitress: Mac and Dennis bribed the Waitress to sleep with Charlie, but Charlie didn’t advance toward the Waitress. Mac and Dennis were disappointed. (“Charlie Has Cancer”). Later on, he was not quick enough to say anything to her when she claimed, “I’m going to bang the next person who talks to me,” before Schmitty popped in (“The High School Reunion, Part 2: The Gang’s Revenge”). She was saying that she was going to bang the next person who talked to her.
It was not shown whether or not Charlie banged one or more prostitutes while celebrating with Frank’s money, so it is unknown whether or not he did so. Mac vouched for the truth of the statement that “…services have already been rendered.” (“Dennis and Dee Go on Welfare”).
Even though they had been engaged briefly, Sun-Li followed him home and moved into his apartment. He did not even kiss her. After further investigation, Charlie learned that she was only 12 years old. (“The Gang Solves the North Korea Situation”).
Painted females at the fraternity
Painted females at the fraternity — two girls painted Charlie and Mac, and they intended to let them return the favor before taking a shower together to remove the paint from their bodies. (presumably leading to sex). However, before Charlie and Mac could color them again, the fraternity’s leaders expelled them. (“The Gang Reignites the Rivalry”).
Charlie, known for his self-indulgent behavior, was busted masturbating by multiple group members. Masturbating Dennis’s cartoon drawings of women with large breasts, Dee captured him in the act. (“The Aluminum Monster vs. Fatty Magoo”). She accused him of stealing Dennis’s erotic memoir to masturbate to its photographs to make up for the fact that he could not read the biography’s text. (“Dennis Reynolds: An Erotic Life”). Frank also mentioned that one of his favorite things to do is to hide inside the couch in Charlie’s apartment to capture him “pounding off.” (“A Very Sunny Christmas”). When Charlie tells Frank that he woke up to him doing some “pretty frantic research of [his] own” one night, Frank responds by stating that the two of them could “go tit-for-tat on that one.” Charlie reveals that he awoke to Frank doing some “pretty frantic research of own” (“Mac Is a Serial Killer”).