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While trying to get an endorsement from the Chief of Police, Leslie and Ben awkwardly run into Leslie's old flame, Dave. Meanwhile, Andy and the rest of the office work on a theme song for Leslie's campaign.
It's Valentine's Day and Leslie decides she needs to find Ann a new man. Ben must enlist Ron's help when he is stumped by Leslie's elaborate Valentine's Day scavenger hunt, and Chris is depressed about the status of his love life.
Leslie realizes that the department has forgotten Jerry's birthday and decides to throw a party for him at a special location. Meanwhile, Tom is flabbergasted when he finds out Ann doesn't share his taste in music.