Mary's future may be resolved, but the rumor mill surrounding her situation runs rampant. While ugly rumors spread about Mary's sudden departure, Simon is persuaded to use his sister's bad reputation to boost his 'cool' quotient at school and gets into some trouble of his own with identical twin bad girls, Carol and Sue Murphy (Mary Kate and Ashley Olsen, Full House). Congregational gossip irks Eric. Lucy wrestles with high school hearsay. Ruthie spreads phony tales to draw attention away from Mary, and Matt's infatuated with a beautiful stranger. Also, Annie goes out with an old boyfriend.

Annie discovers that the particularly flirtatious mother of one of Lucy's friends, Serena is seeing Eric for therapy sessions. Annie strongly requests that he refers her to someone else. Annie then has to deal with the guilt over her jealousy-induced interference between the two. Also, Simon is mortified when word gets around school over the fact that he's a virgin. Annie had shared the details of Simon's sexual inexperience with his ex-girlfriend's (Sasha) mother, Rita. Meanwhile, Matt struggles about telling Robbie he's interested with his ex-girlfriend, Cheryl. Lastly, Robbie is also hiding a secret from Matt that involves his ex-girlfriend Heather.