Kevin hires a tutor for Mary-Kate. Ashley convinces Mary-Kate to switch places so she can flirt with Taylor, the tutor, but their scheme doesn't go as planned; Carrie convinces Kevin to ask out a woman at a coffee shop.

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 gets assigned Pokey Valentine, her crush, as a partner on a history project. She becomes jealous when Pokey and Mary-Kate begin spending time together.

When Kevin starts dating a woman, Marci, they fear that she will replace Carrie. The twins scheme to destroy Kevin and Marci's relationship.

Mary-Kate and Ashley switch costumes with Max and Brian so that they can attend Carrie's Halloween party, from which they were banned by Kevin.

Mary-Kate, who has had a bad past with animals, gets a homing pigeon which eventually flies away, causing heartbreak to Mary-Kate.

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

Ashley is excited when a model search for a teen magazine takes place at their school, but Mary-Kate is chosen over Ashley.

After Kevin buys a new telescope, Mary-Kate and Ashley snoop into other people's business. They think they witness their neighbor, kindly old Mrs. Baker, murdering her elderly boyfriend, Mr. Fillmore. The situation gets even scarier for the twins when Kevin asks Mrs. Baker to take care of them so he can attend a jazz concert with Carrie. Meanwhile, Carrie hears Kevin play the saxophone and encourages him to perform for audiences as he used to.

Carrie accepts Kevin's invitation to send Christmas with him and the girls. Carrie brings a homeless man, Walter, as her guest to Christmas dinner. Sometime during dinner, everyone is shocked to find Walter stole all the gifts.

Mary-Kate and Ashley prepare for their first school dance. Mary-Kate wants to dance with Jeremy, but he tells her that he only knows how to swing dance. Carrie teaches Mary-Kate how to swing dance. At the dance, however, they learn that Jeremy doesn't know how to swing dance at all - he lied to her because he doesn't know how to dance.

Mary-Kate and Ashley begin arguing more frequently which causes them to move into seperate rooms. They soon learn that they miss each other and move back into the same room; Kevin's doctor and Carrie begin dating and soon she thinks that Dr. Martinson wears a bra, which leads to an embarrasing moment for both Kevin and Carrie.

Carrie's old boyfriend, Alex Reardon, is back in town and Carrie feels she must make herself look as successful as he is. Carrie convinces Kevin to pretend to be Carrie's fiance to make Alex jealous; The twins have a party which doesn't go quite as planned.