Mary-Kate and Ashley work as matchmakers to get Mrs. Baker and Mr. Fillmore together so that Carrie, a student of Kevin, will be hired as their new baby-sitter.

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.

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.