Ann befriends an African-American boy after saving him from a shoplifting charge. When he tells her he lives on Park Avenue, she does not believe him, so he invents a story of 13 brothers and sisters, fat rats, life in a dirty tenament, and a father who beats him. Appalled, Ann goes so far as to decide to adopt him! The boy then calls his father, who happened to be wealthy like he said earlier.
On Valentine's Day, Ann and Donald exchange permanent gifts. She gives him a tie clasp and he gives her a pair of genuine diamond earrings they saw together at Tiffany's. Ann is scared to wear them. When Don puts his foot down and insists she wear them on their evening of dinner and dancing, one of them indeed disappears. Don buys her a replacement earring and puts it in her apartment. Ann, not wanting to disappoint Dan, buys a replacement earring herself.
Ann and Donald decide to take a little vacation from themselves, so Ann decides to move into her parent's house. Her parents are going on vacation, and she stays there. A noise gets her locked down in the basement and she is trapped. Her parents are worried when Ann doesn't answer the phone and they hurry back home to find that Donald has rescued her.
When an aggresive bully collides with Ann in an office lobby, only nearby window washer, Rudy Clarn comes to her aid. But while warning him off, the bully slugs Rudy and breaks his nose. Feeling terribly guilty, Ann helps him to the doctor and then home. Rudy's wife, Ethel - a terribly jealous woman, believes there is more to the relationship between Ann and Rudy and threatens to leave him.
Donald's sexy new secretary, Pat Crawford, arranges to accompany him on an out of town assignment to Washington, D.C., hoping to steal his heart from Ann. Feeling neglected and rejected, Ann decides she'll spare Don the pain of breaking up with her and she'll have it all done by the time he returns, so she returns all borrowed items of hers and Donald's to their proper apartments. But when she discovers she was wrong, she has only minutes to get everything back to normal before Don finds out.
Ann is excited at the prospect of voting in her first presidential election. She's gone to the library to read everything she can about the issues and the political process. But on Halloween night, when Ann's father asks her what party she registered with, Ann feels it's her right to preserve her secret ballot.