Tim thinks wearing a Cinderella dress during March Madness is good luck, so he refuses to take it off in hopes his alma mater will win. Also, Greg fantasizes about what to write in a birthday card for his boss, Tyler goes to prom and must withstand unsolicited advice from his parents and grandparents, and Jen sets Matt up on a blind date with her coworker, Dougie.
- Colin Hanks as Greg Short
- Betsy Brandt as Heather (Short) Hughes
- Thomas Sadoski as Matthew "Matt" Short
- Zoe Lister-Jones as Jennifer "Jen" Collins-Short
- Dan Bakkeddahl as Dr. Timothy "Tim" Hughes, M.D.
- Angelique Cabral as Colleen Brandon Ortega
- Niall Cunningham as Tyler Hughes
- Holly Barrett as Samantha "Sam" Hughes
- Giselle Eisenberg as Sophia Hughes
- James Brolin as John Bertram Short
- Dianne Wiest as Dr. Joan (Pirkle) Short
- Hunter King as Clementine
- Jerry Lambert as Chase
- Fortune Feimster as Dougie
- Meera Rohit Kumbhani as Milly
- At 17:03 when the bowling scoreboard is shown, Matt's game was not scored correctly. His Total Score of 47 should have been 54. Frame #7 (a spare) should have added 17 instead of 10.