After an accidental meeting, two New Yorkers decide to go on a date where they each bring a friend.

Romantic obstacles abound during Kate and Ben's first official date.

Ben looks for a birthday present for Kate; Connie plans a lavish birthday party.

Kate is overprotective when her younger sister, Julia (Brittany Snow), visits New York for the first time; Connie and Larry try to help each other pick up dates at the bar.

Ben tries to impress Connie by assisting her at work; when Kate learns how Larry ends relationships, she intends to change his ways.

Kate spies on Ben when he is required to work late nights with his ex-girlfriend; Larry tries to track a mysterious woman.