Yes, Dear Season 1 Episode 11

All I Want for Christmas Is My Dead Uncle's Cash (a.k.a. Silent Night, Holy Crap)

Jimmy finds out that his mean Uncle Elton died and left him $5000. Jimmy takes half of it and tells Greg and Kim he'll be paying them back the money he owed them to get set up in L.A. Afterwards, Jimmy and Christine go Christmas shopping with the other half. Despite Christine's protests, Jimmy sees two expensive Lionel train sets and wants to spoil Dominic for Christmas, but can't decide which one to get. So he gets both. But when he visits with his uncle's lawyer to claim his inheritance, Jimmy learns the bad news -- he doesn't get $5000, he gets $5000 less taxes. And he's now overdrawn before he's even paid Greg back. With no other choice but to get a second job to cover his debt, Jimmy lands work at the toy shop where he bought the trains. And where he now has to answer to the smug manager he was rude to previously. If that's not embarrassing enough, Greg bumps into Jimmy while he's on the job in a silly reindeer costume. Jimmy comes clean, and Greg demands that he just take the mon