Andy finally meets the perfect girl, but things get rough when he lets Jim babysit the woman's daughters, who then end up missing while Andy is having dinner with Emily.

Dana puts Andy under hypnosis to learn why all of his relationships don't last longer than six weeks. Upon learning that it's due to Andy's low self-esteem, Dana decides to boost up Andy's confidence, but she ends up making things worse when Andy starts flirting with other women while on a date with Emily.

When Dana, Cheryl's sister and best friend, moves away, Jim realizes he must find Cheryl a new friend as soon as possible.

Jim urges Andy to propose to Emily or risk losing her, but when he sees Emily dining with another man, he doubts the wisdom of his advice.