After Kate and Ben fall in love at the Empire State Building they want to see if they can help their best friends Larry and Connie can get a taste of the love bug. They may regret that decision because at the moment Larry and Connie can't stand 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.

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.

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.

Ben unfortunately has to work late nights with his ex-girlfriend to alleviate her worries Kate uses the cameras to make sure that Ben isn't cheating on her. Larry is along with Kate to use the cameras to find a potential date.

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.

Larry takes getting out of a traffic ticket to a new level, he intrudes on Connie's date. After accidentally losing her bosses dog Kate hopes she still has a job to go back to after her boss finds out what happened.

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.

Tiffany sets things in motion after having to leave New York because of the divorce she went through. Unfortunately and for Connie and it means and she has to find a new job and Larry and may finally get to date the girl of his dreams.

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.