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 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.