Jane, a bit tired of being a third wheel to her best friend and ex-boyfriend, winds up meeting a cute guy named Nathan at a thrift store. Nathan is into a retro clothes fad, and Jane soon becomes involved too. Daria and Tom don't really like Nathan, but Jane is similarly put off by their discomfort. However, they're eventually proven right when Nathan and Jane get into a fight, which demonstrates that Nathan is a bit too obsessed with this gimmick. Jane breaks it off and sells her retro clothes (most of which she just found in the attic) for a tidy profit.
A subplot involves Upchuck showing off his magic tricks, which intrigue Stacy so much that she volunteers as his assistant. The pair get a gig at the school, where Upchuck will be locked in a box and forced to escape; naturally, a large part of the student body buy tickets for the chance to see him perish. Sure enough the stunt seems to go wrong, and Stacy has a breakdown on stage; however, it turns out that this was part of the act, and when the school's staff finally gets the box open they find it empty, with Upchuck calmly standing in the audience.
Tropes present in this episode:
- Awesome Anachronistic Apparel: Nathan intentionally dresses in 1940s-50s styles, and he looks fine enough to date Jane.
- Decade-Themed Party: Jane is dating a guy, Nathan, who is obsessed with swing dancing and the styles and manners of The '40s. They go to a dance party and to a drive-by cinema meeting centered around the decade.
- Disco Dan: Nathan is a high schooler obsessed with 1940s aesthetics.
- The Dog Bites Back: Continues the season five trend of Stacy growing a backbone and standing up to Sandi and the other Fashion Club members.
- Fan of the Past: Nathan love The '40s and enjoys swing dancing and generally the decade's style and flair.
- Ironic Echo: Stacy and Sandi mock each other with this when bickering about Upchuck, "Oh, Stacy/Sandi; you're so naive."
- Limited Wardrobe: Lampshaded; Jane's looking at everything in her closet and comments that this was a lot easier when she just wore the same thing every day.
- Nobody Touches the Hair: When kissing Nathan, Jane messes up his hair and he has a minor freak-out.
- "Oh, Crap!" Smile: Stacy does this when she doesn't know what to do after locking Upchuck in the box. It’s possibly an act.
- Running Gag:
- Daria, Jane and Tom each make a joke suggesting that Daria will eventually date Nathan like she's dating Tom; each time, the other two act surprised/offended.
- Ms. Li repeatedly tries to use subliminal messages to get the students to tithe to the school.
- Serious Business: Nathan takes his nostalgia to a rigid and ridiculous degree, to the point he feels like micromanaging what Jane wears and does. Jane tells him to lighten up because this is just for fun, while Nathan feels he's a true believer who has to stand his ground against "trendies."
- Skewed Priorities: During their discussion about Jane’s shoes that initiates a whole fight about their differences, Jane tries to make a point saying that he’s supposed to like her whether she dresses up or has sweatpants. Nathan replies with disdain “You own sweatpants?”. This is the last straw for Jane and she dumps him.
- Stage Magician: Upchuck gets attention by showcasing magic tricks at the mall. Ms. Li decides to use him as another fundraiser.
- Unlimited Wardrobe: Lampshaded; Jane goes through several different outfits in this episode. At one point she's looking at everything in her closet and comments that this was a lot easier when she just wore the same thing every day.
- Wham Line: After Sandi "assures" Stacy that Upchuck suffocating to death means she won't have to spend her life getting revenge on him for her humiliation.Stacy (who is abruptly stopped crying): Oh Sandi, you are so naïve.
