Sparks fly between Caroline and Randy when he pays her a surprise visit in New York and they end up getting stuck together in a subway tunnel for two hours. Meanwhile, Richard gets his first real break as an artist when an eccentric gallery owner offers to exhibit his work -- but only if he can create another 'bleak' painting in time for the next day's show.

Caroline accepts Richards marriage proposal. However, they have very different ideas about how the wedding will go. Richard drops a bombshell when he reveals that he has a son from his brief marriage to Julia. They decide to go to Italy.