S05E19 — Virgin

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.