Caroline gives Richard a matrimonial ultimatum; but on his way to propose to her, he is taken hostage in a video store holdup. He decides that escape will prove his manhood and worthiness of Caroline -- and when he is wheeled in by paramedics, he does indeed propose.
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 and the gang visit her family's home in Wisconsin and learn her parents are selling the house. Distraught, she prolongs her stay (while Richard unwillingly bonds with the locals), and ultimately decides to preserve her childhood memories by buying the house herself.
Caroline tries to right an old wrong by giving up a romantic weekend in Boston with Richard to help out a visiting childhood chum, Joanie, whom Caroline once bullied in school. Meanwhile, a lonely Annie finds unexpected companionship with a smooth-talking parrot when she agrees to bird-sit for Dave, and Del has trouble accepting the fact that his new girlfriend Lisa is taller than he is.
On Halloween, Caroline and Richard go on their first date, but she's disappointed when she thinks he didn't plan anything special; Del fears he's going to be fired. MacDermott: Edmund L. Shaff. Zorro: Clint Carmichael. Caroline: Lea Thompson.
Caroline settles into her new workplace, where she inadvertently - and immediately - ticks off office manager Plum, who banishes Caroline and Richard to the basement. Meanwhile, Annie lusts after her yoga teacher Jonathan, but learns from Angie that he is a former porn performer.
Caroline in the City is an American situation comedy that ran on the NBC television network. It stars Lea Thompson as cartoonist Caroline Duffy, who lives in Manhattan in New York City. The series premiered on September 21, 1995 in the "Must See TV" Thursday night block after Seinfeld. The show ran for 97 episodes over four seasons, before it was cancelled; its final episode was broadcast on April 26, 1999.