In Brooklyn Nine-Nine Season 1, Episode 13, "The Bet," Jake Peralta wins a year-long arrest competition against Amy Santiago, resulting in a "worst date ever" stakeout. The episode serves as a turning point for the characters' relationship, as Jake realizes his feelings for Amy, while Charles Boyle receives the Medal of Valor while heavily medicated. Read more at the Brooklyn Nine-Nine Wiki . "Brooklyn Nine-Nine" The Bet (TV Episode 2014) - IMDb

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[s1e13] The Bet Site

In Brooklyn Nine-Nine Season 1, Episode 13, "The Bet," Jake Peralta wins a year-long arrest competition against Amy Santiago, resulting in a "worst date ever" stakeout. The episode serves as a turning point for the characters' relationship, as Jake realizes his feelings for Amy, while Charles Boyle receives the Medal of Valor while heavily medicated. Read more at the Brooklyn Nine-Nine Wiki . "Brooklyn Nine-Nine" The Bet (TV Episode 2014) - IMDb