When the Arnolds attend the wedding of Jack's boss' daughter, one of the bridesmaids turns her attention to Kevin. He tries to get a bottle of champagne for them to consume together, but ends up drinking it while he waits for her. When she does arrive, Kevin vomits on her. Later, Wayne tells Kevin that he's had sex with the bride.

Kevin wants to earn some money to take Winnie out for dinner, so he jumps at the opportunity to paint his sociology teacher's house. When he tries to con some younger students into helping him out, things start to go wrong.

Some people never find true love, but Kevin believes he did. He had what most people search all their lives for, but he blew it. When Winnie comes over for a study session while his parents were away, Kevin wants to relationship to go further. Winnie sees through his plan. She does stay, but they just fall asleep together. The next day, though, he tells his friends a different story. When Winnie finds out, she dumps him.

Wayne seems to be a changed man, considering his relationship with Bonnie and her baby. Kevin longs for a romantic vacation with Winnie, but must face reality on New Years Eve when Bonnie leaves Wayne for her ex-husband.

Over a game of poker we learn some truths about Kevin's friends, including that Chuck thinks he's gotten Alice pregnant, that Randy is worried about failing trigonometry and that Paul and Kevin are drifting apart.