- In "Gotcha Day", Ravi explains to the gang that when he was adopted, he didn't know that the Ross parents was expecting for him to be a baby because his room has a crib bed, stuffed animals, and diaper bags. When he finds out, thanks to Jessie, he thought he was just a disappointment to the family. Him running away upset is pretty heartbreaking especially if you did the same thing!
- In "Messy Dress", NBA Chris Bosh's confidence is shot to the point he lost his basketball skills because his lucky socks were washed. This is supposed to be funny, but seeing the professional sports player loses his edge is sad for some. If Jessie didn't snap him out of it, he'd have lost his career forever.
- Chris Bosh is hardly the best actor in the world, but his deadpan delivery actually helps drive home how devastating it is for him.
- The episode where Jessie is trying to wean Luke off his stuffed koala he tells the family he has a hard time giving him up because it was all he had at the orphanage.
- The fight between Jessie and her dad in the Season 2 finale:Mr. Prescott: It's a lot easier to be supportive when you make good decisions!
Jessie: Leaving home was a good decision!
- Arguably, the season 3 finale. (Not going to spoil it for those who haven't seen it, but a lot of it is pretty sad, from the kids thinking that Jessie is going to leave them forever to Bertram giving Jessie away in place of her father.
- The series finale isn't really this until the end when Jessie is moving to Hollywood and Christina is going to be a stay-at-home-mom and the goodbyes between Jessie and Bertram and the kids. Especially the kids.
Tear Jerker / Jessie