Ben and Kate each worry that they are each not "fun" enough in the relationship and try to prove to the other that they are. However, after a spontaneous trip to Staten Island, things start to go very wrong. A series of events lead to Ben's clothes being stolen, along with his money and cell phone and they are challenged to make their way back to the city so that Ben can give a big speech at a legal conference, for which he is unprepared. Meanwhile, Larry runs into Connie in his office building and tags along to her meeting to pitch a children's book in order to flirt with Tiffany. Ultimately, Ben and Kate are able to reach Larry and Connie who meet them in time to loan Ben one of Larry's suits and Ben finds that even without his speech, the day with Kate is inspiration to help him wing it successfully.