Air date: 12/7/95

Annie dates Steven, an ex-convict. He burglarizes Caroline's apartment, and steals one of Richard's paintings.

Caroline and the Christmas Break

Air date: 12/14/95

Del and Caroline plan a trip to Paris, but after opening his big mouth Caroline decides to break up with him.

Caroline and the Gift

Air date: 1/4/96

Caroline believes Del bought her an expensive gift, which turned out be much more modest than she thought. Richard paints a nude of a Mobster's girlfriend. Annie tries to find a man she met at a New Year's Eve party.

Caroline and the Married Man

Air date: 1/11/96

Richard sets Caroline up on a date in order to increase his chances of getting an art commission, but it backfires upon realizing that he is married.

Caroline and the 28lb. Walleye

Air date: 1/25/96

Caroline returns to her hometown of Peshtigo, Wisconsin, where a park is dedicated to her. Her brother Chris steals the limelight away from her once again, however.

Caroline and the Watch

Air date: 2/1/96

Caroline buys an antique desk on the way to the deli, and later finds a watch gift wrapped inside. She tracks down the old owners.

Caroline and the Bad Date

Air date: 2/15/96

Annie convinces Caroline to ask out a man shopping for shirts at the mall. He turns out to be paranoid. She meets Del at Remo's and they sleep together.

Caroline and the Proposal

Air date: 2/22/96

Caroline decides whether or not to accept Del's marriage proposal. Remo and Annie tell her Richard has feeling for her. Richard visits a temp agency looking for work.