Milly Molly was generally a happy cartoon and book series, but when it was sad it was very sad.
- The whole episode "Grandpa's Oak Tree". An elderly couple named Granny and Grandpa Peg die of old age, while their sacred tree is about to be chopped down to make way for a road. It makes it even worse that the narrator is being poetic instead of just narrating.Narrator: "After Milly & Molly went home, a happy, but tired, Granny Peg put a very last log on the fire and climbed into her nice warm bed she used to share with Grandpa. That night, Granny Peg began her journey to be with Grandpa once again."
- Dr Smiley telling Grandpa that his days are numbered, right after Molly has said he can't get up and didn't laugh and the girls, serious-faced, went to fetch the doctor...
Dr Smiley (looking uncharacteristically serious): "You have to think about Granny Peg. She'll live to be a hundred, but"Grandpa: "But I won't How much longer have I got?".Dr Smiley: "You may not see another winter".- And then there's Granny looking sad.
Granny: (tearful) "Oh, Grandpa...Grandpa finally wore out last night" - Milly getting chicken pox on her birthday.
- And later, Humphrey gets chicken pox. This is less sad as it's a background moment.
- Sometimes, things can be sad when you fear something bad will happen to an animal or person.
- And in "Horse Power", when there's a drought and Farmer Hegarty worries that he will have to sell Salt and Pepper the horses.
- In "Marmalade and the Birds", when Milly is worried that Marmalade will have to leave home.
- In "Goodbye, Alf", they were worried Alf and his nan were going to move away.
- "Wags". When Wags was dog-napped, they were worried about him.
- When Marmalade and Tom Cat's children were kittens and the girls feared their dad would throw them in the river. Of course, he didn't.
- The Feud Episode "Cubby House". Things get better, at the end, but it gets pretty sad. This line says it all.Narrator: "Poor Tom Cat thought they were going to Milly's place to see Marmalade, but alas, Milly and Molly weren't friends anymore".
- Gertrude, a.k.a. "Sooty", the cat who broke her leg, can be a woobie.
- So can Alf and his nan. They are poor and they used to be from another country that Alf doesn't want to talk about. Also, Alf's father died when he was a baby.
- The whole episode "Goodbye, Alf". Alf and his nan might move away and Pepper the horse has a serious illness.
- The book "Jimmy's Seeds". Jimmy, a classmate of the "M"s, is absent from school and then it's revealed that he died.
- When it's revealed that Jock the budgie died.
- Goldie the fish dying in the book "Milly, Molly and I Love You".
- Aunt Maude and the girls getting the measles in "Biddy Bid".
- In "Aunt Maude", when Maude's leg breaks. And then Milly, Molly and a bunch of others get sick.
- Mr Limpy's Priceless Ming Vase that used to belong to his departed wife breaking.
- When Molly strains her voice. Yes, she recovers and she's not sick and nothing goes wrong with the concert, but there's this line.Molly: "This is the worst thing that's ever happened to me".
- Molly's doll Dolly being missing in "Lost & Found". Particularly, when several times it implies she might not get her back. She does.
- Milly missing Molly in "Class Concert".
