"Here are some things you want to hide about yourself on tonight's date—you're cheap, you're a heavy drinker, you're broke, you have a problem with anger."
— Schmidt
Nick and Jess try to go on a first date; Schmidt and Winston try to sabotage it.
Tropes in this episode:
- Artistic License – Law: This episode's Running Gag has Nick repeatedly ticketed for jaywalking when he tries to walk across an empty street. Jaywalking only applies if you're obstructing traffic or disobeying signs.
- Cannot Spit It Out: At the end, Nick and Jess are caught in stasis between open attraction to each other and each waiting for the other to make a move — Jess is confused about where they stand because he never outright states what he wants out of their relationship, Nick seems to know exactly what he wants but is too nervous to act in case Jess doesn't feel the same way, which just confuses her further, which...
- Gilligan Cut:Nick: I’ve gotta be confident. I’ve gotta be clear. Women like that. I just gotta say, ‘Jessica, you are a beautiful woman, and my life has not been the same since I met you. And it would mean the world to me if you would go on a date with me.
[cut to him outside Jess's door]
Nick: Jess. Uh-cah. Dirty J. Doctor Day. Mah toilet sister! If so, food? - Hobos: "Outside Dave", a homeless man who lives outside their loft, is enlisted to ruin the date but he gets too comfortable in the apartment.
- Impossible Pickle Jar: Jess can't open jars, and Nick is apparently turned on by this.
- Line-of-Sight Alias: Nick's new girl? Yolanda...Winston. Schmidt and Winston immediately conclude it's a fake name and he's taking Jess.
- The Makeover: Nick enlists Schmidt and Winston to prep him for his date; Schmidt gets him a suit and Winston does his facial hair (and even lets him borrow his new car).
- Running Gag: The characters keep getting caught for jaywalking.
- Shipping Torpedo: Schmidt (and to a lesser extent Winston) are opposed to the idea of Jess and Nick dating and try to ruin their date. However, their attempt to sabotage it turns into an effort to get a hobo out of their apartment.
- The Unreveal: Russell asks both Nick and Jess to write what they think this night was on valet tickets. He doesn't reveal what either of them wrote, saying it's a bad idea, lending a sense of ambiguity to the whole evening that isn't lost on the two.
