When Ben Parr and Kate Swanson accidentally meet at the top of the Empire State Building, they make a date for later that evening and each bring along their best friends, Larry and Connie, who instantly despise each other.

Ben and Kate's first official date is fraught with romantic obstacles, most notably Larry and Connie.

As Ben tries to find the perfect birthday present for Kate, his advice to her may ruin her friendship with Connie, who is busy planning a lavish birthday affair.

When Kate's younger sister, Julia, makes her first visit to New York, an overprotective Kate seems to forget that Julia is no longer a little kid. Meanwhile, Larry and Connie decide to be each other's wingmen at the bar.

Ben is determined to win Connie over by helping her at her nanny job, while Kate tries to change Larry's ways after she learns that he breaks up with women by avoiding them until they leave him.