Yup, Jake and Amy are on a date in this Brooklyn Nine-Nine scene. That's what happens when you lose a wager.
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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.
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Brooklyn Nine-Nine Season 1 Episode 13 Quotes

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

Charles

Amy: Don't say money because I know you're in debt.
Jake: Well, if you really knew me, you'd say crushing debt