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.