9. James Rolf High School Twentieth Reunion

Ron decides to cater his own high school 20th reunion, hoping to impress his former classmates—especially the event organizer Melinda ( Molly Parker )—that he's a team leader and that he's not like how he was in high school. Constance's roommate Bobbie St. Brown ( Jennifer Coolidge ) takes over her position in the Party Down team. Henry thinks of moving back home with his parents, but Casey is able to convince him to stay as they rethink their relationship. Ron tries to ignore his former best friend from high school ( Joe Lo Truglio ), to try sell his new image to Melinda. After Ron interrupts Melinda and Mark Defino ( Kyle Bornheimer ) in an intimate situation, he slips back into his old ways by trying to drink an entire bottle of whiskey like he previously did in high school, and subsequently vomits while trying to get someone to call an ambulance.