A distressed Milo turns to Pepper Ann for help in becoming more manly after realizing that spending time with girls has made him a laughingstock among his peers.
Milo is upset that he cannot attend a gender specific assembly, but Pepper Ann and Nicky tell him that it does not matter as it is just about female hygiene and bring up the fact that last time he tried to sneak through the air vents to listen. While he waits for them, Milo claims that he will hang "with the guys" which confuses them as Milo does not have any guy friends. He goes to various groups who are quick to turn him down due to his feminine tastes. Milo panics and tells Pepper Ann and Nicky that he needs to know what it is like to be manly, so Pepper Ann decides to take on the challenge of manning up Milo. Throughout the episode, Pepper Ann imagines "creating" Milo similar to Dr. Frankenstein creating his monster.
They first go to Mr. Finky for advice on being manly, but Milo ends up getting him to cry over his relationship. Pepper Ann then tries to get Milo into football, but he is badly beaten by the game. Milo wanders home where he has a conversation with his step-dad Dirk about being a man, but he cannot hear over his mowing. While getting Milo to read men related magazines, Nicky tries to explain to Milo that by him being "less of a guy actually makes him more of a guy", but he takes it as a demeaning statement. Pepper Ann sets Milo up against the bully to fight, but Milo ends up bringing him peace.
Milo gives up on being a man and heads to the locker room. All the other guys start talking about girls and admit that none of them are "man enough" to really know anything about them. Milo intervenes and gives his take on girls, "They think you shouldn't call them chicks for one thing," and then proceeds to give a lecture on the mindset of girls. Afterwards, Milo admits to Pepper Ann and Nicky that he is happy for who he is and now gets supportive attention from all the other guys in school. Pepper Ann is at first saddened that she was unable to help Mil, but perks up upon realizing that Craig Bean was among the boys that got advice from Milo.
- Kathleen Wilhoite as Pepper Ann Pearson
- Jeff Bennett as Craig Bean, Dieter Lederhosen, Additional Voices
- Danny Cooksey as Milo Kamalani
- Clea Lewis as Nicky Little
- Jim Cummings as Mama Tried, Dirk
- Don Lake as Sherman Finky
- Jenna von Oÿ as Trinket St. Blair
- Nicky pokes fun at the concept of perspiration being taboo as it is technically something that is natural.
- Nicky becomes aware of Pepper Ann's continuous habit of accepting unnecessary that is clearly beyond her limit of understanding.
- The episode implies that Mr. Finky was or might be in a relationship with Ms. Sneed as Milo states that she expressed her love through her knitting.
- The episode makes a somewhat lewd joke. When Pepper Ann gives Milo a series of Men related magazines to look through one of them is an issue of Play Dude. Embarrassed, Pepper Ann responds, "How did that get there?" The magazine is a reference to Playboy Magazine which is known for its adult content directed at men.