At his parents' suggestion, Patton joins the wrestling team, but has to wrestle a girl; Parker and Penny go for a joyride. Wendy: Iyari Limon. Carmen: Vanessa Anne Hudgens. Jill: Sarah Campbell. Ref: Matt Baker. Patton: Ryan Pinkston.
Bob takes Penny and Paige to visit their great-aunt (Phyllis Diller); Parker gives Pearce some tips on romance. Alayna: Alice Greczyn. Bailey: Shannon Woodward. Gilbert: Kevin Christy. Philip: John Reha. Pretty Girl: Krista Kalmus. Bob: Andy Richter.
Paige convinces Alayna (Alice Greczyn) to spend time away from Pearce, who takes it poorly; and Patton and Penny double date. Matt: Robert Hoffman III. Brady: Daniel Kountz. Julie: Nicole Paggi. Manicurist: Sarah Chang. Waitress: Audrey Baranishyn. Sophia: Sandra Purpuro.
Bob and Carol go to Atlantic City to try to win money to celebrate Christmas with the quints; and Pearce becomes an elf for the holidays. Director: Heather McDonald. Julia: Alicia Ziegler. Kelsie: Rachel Style. Marcello: Nathan Lee Graham. Santa: Mark Holton. Bob: Andy Richter.
Carol becomes friends with Parker's girlfriend (Sara Paxton); Patton and Pearce double date with a girl and her dog. Eliza: Davida Williams. Hostess: Renee Forsman. Hugo: Samm Levine. Great Looking Hugo: Travis Van Winkle. Waiter: Trevor Neubauer.
Bob's sports-agent brother (Jason Priestley) visits for Thanksgiving and brings Bob to a nightclub in hopes of signing Amanda Beard (appearing as herself), the Olympic gold-medal swimmer. Bob: Andy Richter.
Patton and the Coach (Patrick Fabian) vie for the attention of a teacher (Tara Reid); Bob tutors Pearce on writing an English paper. Ms. Kilcoyne: Kristin Bauer. Mrs. Wilcox: Francesca P. Roberts. Patton: Ryan Pinkston. Pearce: Johnny Lewis. Bob: Andy Richter.
Bob asks Patton to pretend to be a 10-year-old so that he can be a playmate for a client's son; Parker and Pearce split a date with Alayna (Alice Greczyn) without her knowledge; Penny takes a job where Paige works.
Pearce and Parker both work on a science project with the attractive Alayna (Alice Greczyn); a girl's attraction to Patton stumps others. Pearce: Johnny Lewis. Parker: Jake McDorman. Patton: Ryan Pinkston.
Paige celebrates a longtime friend's return from Africa with a slumber party, and Patton tries to spy on the festivities. While Parker finds himself attracted to the girl, she likes Pearce. Paige: Sarah Wright. Patton: Ryan Pinkston. Parker: Jake McDorman.
Penny is chosen to direct the school play, “Romeo and Juliet,” and her siblings pitch in with Patton cast as the male lead. Ms. Hentschel: Harriet Sansom Harris. Amy: Jacqueline Lord. Brad: Billy Gardell. Carrie: Danica Stewart. Crazy Pete: Aaron Pinkston. Lynn: Heidi Marnhout. Matt: Robert Hoffman III. Bob: Andy Richter.
Penny loses her date for the homecoming dance to Pearce, while Parker's stuck with a bully's sister and Paige wants to be selected queen. Matt: Robert James Hoffman III. Gina: Brooke Lewis. Tyler: Adam Grimes. Brittany: Ja Nee Nisonger. Carrie: Danica Stewart. Catherine: Christina Cindrich.
The quints get jobs: Paige and Patton work in a shoe store, Parker at a fast-food joint, Pearce at a pet shop and Penny (briefly) at a book mart. Alison: Candace Kita. Amy: Jacqueline Lord. Brad: Billy Gardell. Bob: Andy Richter.
The flu strikes the Chase family and, one by one, the quints are quarantined in the basement. Bob: Andy Richter. Carol: Rebecca Creskoff. Paige: Sarah Wright. Parker: Jake McDorman. Patton: Ryan Pinkston. Pearce: Johnny Lewis. Penny: April Matson.
While their parents (Andy Richter, Rebecca Creskoff) are at a Bruce Springsteen concert, the quints decide to throw a party. Paige: Sarah Wright. Parker: Jake McDorman. Patton: Ryan Pinkston. Pearce: Johnny Lewis. Penny: April Matson.