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 aren't able to go on their first date because Larry and Connie are keeping them from it.
Ben gives bad advice to Kate not realizing that the advice could ruin a friendship that Kate and Connie have as well as the party being planned for Kate's birthday.
Kate welcomes her younger sister Julia for a visit and doesn't realize that her sister is all grown up. Larry and Connie decide to support each other 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 spies on Ben when he is required to work late nights with his ex-girlfriend; Larry tries to track a mysterious woman.
When Kate crashes Ben's car during a road trip, the gang is forced to share a room for a night.
While Larry intrudes on Connie's dates with Officer Barrett in an attempt to get out of a traffic ticket, Kate fears for her job when she accidentally loses her boss's dog.
An obnoxious client forces Ben and Larry to jump through hoops before he gives them his business. Larry risks the account - and his friendship with Ben - by choosing to participate in the bar's annual Pub Quiz instead.
When Ben and Kate each worry that they're not fun enough for the other, a spontaneous outing leads to disaster. Meanwhile, Larry tags along with Connie so he can find a chance to hit on her friend.
When Larry loses Connie's camera, she follows him around New York as he retraces his steps, but when they reach the end of the trail, Connie discovers there's more to Larry than she thought.
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.
Kate's ex-boyfriend reveals some shocking information that could put her relationship with Ben in jeopardy, and Connie and Larry's fake date takes a very real turn.
