Zoe is not sure whether or not she has a date with the handsome college student Montana Kennedy. She must befriend his horrible sister Breeny in order to make sure.
Zoe considers having sex for the first time; Zoe's mom lets Duncan camp out on their couch to hide from a girl, but he wakes up in another bed. Elsewhere, Jane and Jack pretend to like each other for their mom's sake.
An old friend (Charlie O'Connell) comes to town and spends his time with Zoe rather than going to his grandmother's 100th-birthday party, which turns out to be her last.
The girls have their first fight after Jane tells Jack about an unopened valentine Zoe wrote to him in fifth grade. Elsewhere, Breeny forces Duncan to be her date.
The group try to get into a new night club despite being underage. A subway sketch artist draws a caricature of the group emphasizing Zoe's head which is drawn as a bowling ball, leading her to obsess that she has a big head.
A stud (Will Friedle) shows an interest in Zoe, but only when no one's around, so her pals dub him her imaginary boyfriend. Elsewhere, the twins plot to break up---then date---Duncan and Lisa (Jacinda Barrett).
Zoe tries to set Iris straight when she chooses to date a mattress salesman (Jim Wise) instead of a hip magazine photographer (Jeff Yagher). Meanwhile, Duncan gets a place of his own---in a storage facility.