Lester is now in his early 30s. He's a substitute teacher and wannabe writer when he meets saucy Ramona Ray (Annabella Sciorra), an art history graduate student. Lester and Ramona seem a dream match. They have common interests, mutual friends and comparable dispositions. The problem for Lester is he just can't stand that there were men in Ramona's life before him. The better they get to know each other and the more Ramona reveals about her past relationships, the more bugged Lester gets. When he thinks about the fact that she went to bed with him on their first date, he even manages to become jealous of himself. In particular, though, he finds himself jealous of Dashiell Frank (Chris Eigeman), a former boyfriend who has gone on to write a best selling collection of short stories. Because Dashiell has accomplished the very thing Lester aspires to, Lester becomes convinced that Ramona would actually prefer to be with Dashiell. Therein lies serious trouble for Lester and delicious comedy for us.

Lester takes to following Dashiell around, and when Lester learns that Dashiell belongs to a therapy group, he contrives to join himself. Only Lester can't actually join as himself. That might somehow lead Dashiell to become reacquainted with Ramona, which is Lester's greatest fear. So Lester joins the group and identifies himself as his best friend, Vince (Carlos Jacott). This plan meets with the real Vince's enthusiastic endorsement. So Lester joins as Vince and talks about Vince's problems, never his own. Complications ensue.