Ashley becomes jealous when, during a slumber party, Mary-Kate reveals that she has kissed a boy; After Paul finds out Carrie was over at Kevin's he assumes their relationship is more than it actually is - which leads to rumors about them being a couple.

Ashley makes a new friend, Nicole, which leads Mary-Kate to feel jealousy; Eddie and Kevin argue while Carrie tries to be a mediator.

Mary-Kate is forced to teach Ashley all about sports when she develops a crush on Eric, a sports fan; Kevin must appoligize to Carrie when he causes waves in their friendship.

Mary-Kate and Ashley places a bet with the school's fund raiser money; Carrie becomes jealous when Kevin starts dating one of her friends.

Kevin realizes that he is bored with his inhibited girlfriend, Nancy, and agonizes over how to end the relationship. When he tries, Nancy misinterprets him and becomes even more serious about him. Matt's advice is of no use, and Carrie is upset because Nancy is her friend. Finally, Kevin gently reveals his true feelings to Nancy, who overreacts. Carrie appreciates that Kevin is sensitive and unwilling to be cruel. Meanwhile, knowing how much Mary-Kate loved horseback riding when her mother was alive, Carrie invites her to come on Carrie's weekly ride. Mary-Kate declines, puzzling Kevin. But Carrie finds out that Mary-Kate secretly visits the stables every day. Mary-Kate admits to Kevin that she doesn't want to remind him of his wife, and he assures her it's okay because it is a good memory. Also, Ashley gets into trouble when she secretly orders a handbag over the Internet using Kevin's credit card.