A newcomer to New York City, Dana is set up on a blind date with Peter, a New York local, who makes a bad first impression.

Things become awkward when Dana bumps into Peter when he's on a date with another woman. Amy encourages Dana to see other people.

When she discovers that Peter is bringing a date to Amy's dinner party, Dana asks her new boss to go with her.

Peter and Dana's idea for an intimate night is disrupted when their reservation at a fancy restaurant is pushed; Amy and David make a substantial decision.

Dana and Peter fight over the movie Love Actually, but when their friends attempt to smooth things over, their plan backfires.

When Peter joins Dana on what he believes is an out of town work conference, she is forced to reveal an embarrassing hobby.