Yup, Jake and Amy are on a date in this Brooklyn Nine-Nine scene. That's what happens when you lose a wager.
Jake and Amy may have the worst date possible on Brooklyn Nine-Nine. "The Bet" is the 13th episode of the show's first season.

Brooklyn Nine-Nine Season 1 Episode 13 Quotes

The last lady I went out with burst into tears when I told her I was a Gemini.


That thing is a date magnet! How many girls have you made out with in that car - six?!