Charlie is stunned to learn his ex-girlfriend is now a man (played by Chris O'Donnell). Original airdate, March 1, 2004.
Tropes:
- Accidental Misnaming: Charlie keeps accidentally calling Bill by his deadname Jill.
- Age-Gap Romance: Evelyn and Bill. Before learning that Bill is transgender, the age difference is what grosses Alan out the most.
- Ambiguously Bi: Bill dated Charlie as a woman and still may harbor some romantic and sexual attraction to him. However, he is also attracted to Charlie's mother Evelyn and dates her.
- Deadpan Snarker: Berta after finding out that Jill is now "Bill", much to Charlie and Alan's displeasure.Berta: What are the odds, huh? One brother turns 'em gay, the other one turns 'em guy.
- Double Entendre: Alan's question to Charlie about Bill turns into this, to Alan's confusion.Alan: Nice guy. Poker buddy?Charlie: Used to. And don't call me "buddy".
- Everybody Has Standards: Evelyn seems fine when she finds out about Bill’s sex-change operation, but passes-out when she realizes that he had slept with Charlie multiple times when he was a woman pre-transitioning.
- Foreshadowing: Charlie talking about Jill, saying that "this girl is something different".
- Girl of the Week: Jill (now Bill) for Charlie.
- Guy of the Week: Bill for Evelyn.
- Hypocrite: Evelyn thinks Alan and Charlie are uncomfortable with her dating a younger man whilst they've dated younger women and calls them out on it. Although she's not entirely wrong considering Alan was against the relationship from the beginning because Bill is younger than him and Charlie.
- If I Had a Nickel...:"If I had a nickel for every time a girl broke up with me and came back as a man, I'd have a nickel!"
- If It's You, It's Okay: Even after learning that Bill used to be a woman and dated Charlie (that last part freaks her out), Evelyn still dates him.
- I Need a Freaking Drink: Charlie's reaction after reuniting with his ex Jill/Bill and learning she is now transgender FTM, is to hit the bottle.
- I Never Told You My Name: One of the things that tips Charlie off about Bill is Bill addressing him by his name. Upon which, Charlie corrects Bill saying he never told him his name as they only just met and asks how does he know his name. It is this that causes Charlie to realize that the man he's talking to is his ex Jill (now as Bill).
- Jerkass Has a Point: Evelyn calls Charlie and Alan hyprocrites for objecting to her dating a younger man when they date younger women all the time. That isn't the real reason they object to it, but considering Alan was against their relationship for that very reason before learning the truth about Bill/Jill, she's not exactly wrong.
- Love Father, Love Son. An odd example. In which, Charlie's ex lover Jill who is now transitioned as Bill is dating his mother Evelyn.
- Love Triangle: Charlie/Bill/Evelyn.
- New Old Flame: Charlie dated a woman named Jill five years prior. When they reunite, he's shocked that Bill is Jill post-transitioning and that he wants a friend for support.
- Old Friend, New Gender: A rare FTM example.
- Out of Focus: Jake only appears in one brief scene.
- Remember the New Guy?: Charlie and Berta discussing his reunion with an old-flame named Jill.
- Shout-Out:
- When Alan realizes that Bill is the same person in the picture of Jill he is looking at, Charlie tells him "Welcome to The Matrix."
- When Bill asks Charlie about the possibility of Evelyn rejecting him upon learning that he is transgender, Charlie calls Bill "Calamity Jane", referring to the homoerotic subtext between the characters Calamity Jane and Katie Brown.
- Smoking Hot Sex: After dinner, Evelyn invites Bill back to her place for coffee and cigars. Bill tells her he doesn't smoke but Evelyn clarifies that he will after they've slept together.
- Trans Equals Gay: Discussed in the episode. When Bill admits to Charlie that he always felt like "a man trapped in a woman's body", Charlie debates that if Bill were really a man, he would've participated in a threesome with him and a cocktail waitress.Charlie: I begged you!
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Trans Character, Cis Actor: The trans man Bill (born Jill) is portrayed by cis actor Chris O'Donnell. - Trans Relationship Troubles: Charlie's relationship with his ex Bill (then Jill) as he broke up with Charlie to find himself. Charlie then complains about the relationship and why couldn't Bill make it work for him. Averted with Evelyn who accepts Bill's transgender secret and still dates him.
