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.
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.
Ben (Jason Biggs) and Larry (Tyler Labine) are excited to defend their pub quiz championship title, until a prospective client (guest star Eric Artell) threatens to keep them from getting there on time. Meanwhile, a handsome masseuse who lifts Connie's (Judy Greer) sagging spirits with compliments about her skin makes Kate (Sarah Chalke) feel old after finding a grey hair on her chin
After Ben (Jason Biggs) convinces her to ditch work for Coney Island, Kate (Sarah Chalke) drags him away to ride the Staten Island Ferry. As their adventure turns sour and threatens to derail Ben's important speaking engagement, Connie (Judy Greer) struggles to impress an editor with her new children's book while Larry (Tyler Labine) is smitten with Connie's boss, Tiffany (Sarah Wright).
When Larry (Tyler Labine) accidentally loses Connie's (Judy Greer) camera and all the pictures she was hoping to use for her book, the search forces him to reveal a secret he's been harboring. Meanwhile, after Ben (Jason Biggs) innocently reveals an embarrassing story about Kate's habits in the shower, Kate's (Sarah Chalke) attempt at getting even causes him to feel self-conscious in court.
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.
