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.

Kate uses the building's security cameras to spy on Ben when he's forced to work late nights with his ex-girlfriend, and Larry tags along in hopes of using the cameras to track the movements of a mysterious woman.

When the gang goes on a road trip to sell Ben's car, Kate accidentally crashes it when Ben says "I love you" for the first time, forcing everyone to share a room for the night.

Connie gets a visit form Officer Dennis Barrett.

When Tiffany decides to leave New York because of her divorce, it means Connie must find a new job and Larry finally has a chance with his dream girl; however, they soon each get more than they bargained for.