When Tyler and Clementine go to a guitar store, Tyler gets uncomfortable when the attractive salesman, Ian, repeatedly hits on her. Also, Tim's tattoo artist, Lois, makes a spelling error on a tattoo he got as a Valentine's Day surprise for Heather, Matt's plan to celebrate Valentine's Day with Colleen doesn't go as well as he hoped, and Greg and Jen discuss whether they should have another baby.
- 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
- Josh Groban as Ian
- Katherine von Drachenberg as Lois (credited as Kat von D)
- Hunter King as Clementine
- Jordan Hinson as Host
- Despite being credited, Holly Barrett and Giselle Eisenberg are both do not appear.
- The shredded cheese Jen is eating out of the bag is a Canadian dairy-free mozzarella flavoured cheese alternative called Daiya.