"Silly old bear."
- During Christopher Robin's goodbye party near the beginning, Eeyore says some genuinely nice things. He even manages to avoid talking about anything sad or depressing (mostly).
- Christopher and Evelyn's Meet Cute in the opening montage. He tries to give her his seat only for someone else to take it, which leaves them uncomfortably close together. It then cuts to the two dancing together in the kitchen, which is easily one of the brighter spots of Christopher’s life after he left for boarding school. Then the next scene happens.
- Christopher Robin arguing against cutting his company's workforce because he promised them good jobs. He may have lost his sense of imagination, but he has never lost his sense of compassion.
- Madeline found the box of treasures the Hundred Acre Woods gang gave Christopher at his going away party. He opens the little pouch Piglet gave him and gives a surprised, delighted little smile.Christopher: Haycorns! I mean, acorns.
- Even though he's well into his adult years, Christopher Robin recognizes Pooh the second he sees him. He kept that promise to "never forget" Pooh. Other stories would have the grown-up deny that his fantastic childhood friend was real; here, he's more confused about Pooh being in London than the fact that he actually exists in the first place. Similarly, Pooh immediately recognizes a fully grown Christopher Robin even when he bears little resemblance to the Christopher Robin he used to know and hadn't seen in years.
- Pooh is also the only one of the inhabitants of the Hundred-Acre Wood who instantly recognises Christopher.
Christopher: Pooh, how ever did you recognize me after all these years?
Pooh: Well, you haven't changed a bit.
Christopher: I've changed tremendously.
Pooh: Not right here. [rubs his eyes with a honey-covered paw] It's still you, looking out. - Once everyone vanishes, Pooh once again heads to the door Christopher Robin would enter through like he's done for the past twenty years. Just as he's about to leave, he suddenly hears young Christopher calling out to him and the door swings open. Pooh walks through the door and ends up in London just as Christopher is at his lowest point and needs him the most.
- Christopher sees his neighbor knocking at his door, hoping to play gin rummy with him now that he's a "time on your hands Tommy", so he runs into the pocket park across the street to hide... so he won't have to disappoint his neighbor by telling him he has to work all weekend. And that's when he meets Pooh.
- This exchange between Pooh and Christopher Robin will simply melt your heart:Christopher Robin: Evelyn warned me!
Pooh: I like to be warmed. Warmed and cozy.
Christopher Robin: I've totally cracked!note
Pooh: (putting his paws on Christopher's face) I don't see any cracks. A few wrinkles, maybe. - When Christopher and Pooh first return to Hundred Acre Woods, it's all gloom and fog. It's only after Christopher falls in the Heffalump trap that it brightens and his friends return. Why? He got scared by Owl's broken weather vane and thought it was a Heffalump. He didn't intend to, but Christopher Robin was imagining. He was playing in the Hundred Acre Wood.
- Christopher's realization that the river under the Pooh Sticks bridge was not as deep as he thought it was and has a hearty laugh once he finds himself in ankle-deep water despite having prepared to hold his breath initially. It's the first time we see the grown-up Christopher look genuinely happy.
- The toys all realize that Christopher Robin needs their help. Without hesitation, Pooh, Piglet, Tigger, and Eeyore go and try to find him in the real world.
- When Pooh, Piglet, Tigger and Eeyore begin their expotition into the real world, the first person they run into happens to be Madeline, Christopher Robin's daughter. While a bit frightened at first, Madeline quickly recognizes Pooh as "the bear from [her] father's drawings", and when Pooh asks for Madeline's help in finding Christopher Robin, she eagerly accepts.
- Later scenes show Madeline getting along with Pooh and co., clearly coming to love them like her father has. At the very least, it is reassuring to see that should Christopher Robin be too busy to see Pooh, his daughter will be there.
- Pooh begs for a balloon, so Christopher Robin buys him one... in his familiar red colour.
- None of the other denizens of the Hundred Acre Wood recognize Christopher Robin at first and they're convinced he's a Heffalump. However, Pooh recognized him immediately.
- How does he finally convince the others he is who he says he is? He goes to "fight" the "Heffalump" that's been terrorizing them. He goes just out of their field of vision and makes an elaborate mock battle with the imaginary beast.
- Eeyore has been dragged along for the ride up until this point and has also been convinced he's a Heffalump. Once Christopher starts pretending however, he squints, and suddenly sees Christopher Robin for real and begins to play along. It's perhaps the biggest, happiest smile Eeyore has given in the entire franchise. Despite all his gloom and doom, he does genuinely love Christopher Robin and missed him.
Eeyore: Christopher Robin, it's you... playin' again. - Christopher Robin and Pooh's reconciliation, with this exchange standing out.Christopher Robin: I'm lost.Pooh: But I found you, didn't I?
- The urgency to get Christopher Robin's work papers back to him is due to Pooh confusing the name of his boss "Winslow" for "Woozle" after Christopher earlier remarked that if he lost them "Winslow will eat me for breakfast!", so Pooh informs everyone that a Woozle is going to eat him if they don't get the papers back to him.
- As the gang is preparing to go through the door to bring Christopher his papers back, Piglet is understandably hesitant to join the adventure.Piglet: Uh, I'm-I'm-I'm not sure I'm going to go. No I think I-I think I might stay. I'm-I'm actually going to definitely stay.
Pooh: (kindly) Oh there, there, Piglet. Come on. Here. [Holds out his paw] We need you.
Piglet: (stunned) You... you need me? [Takes Pooh's hand; they begin to walk through the door] Well, if you need me...
Pooh: We always need you, Piglet.
Piglet: Thank you, Pooh. - Christopher playing "Say What You See" on the train back to London, something Pooh did on the first run.
- On the train, Madeline confesses to Pooh and his friends that she doesn't want to go to boarding school, as her father is insisting is best:Pooh: So why not just not go to boring school?
Madeline: Well, if I can get these papers to Father, then maybe he'll be so happy he won't make me go. Dreams don't come for free, Pooh. You have to fight for them. Nothing comes from nothing.
Pooh: [Chuckles] Oh-hoh yes, doing nothing often leads to the very best something.
Madeline: What? Who told you that?
Pooh: Christopher Robin.
Madeline: [Puzzled] That doesn't sound like Father.
Pooh: He also said your happiness means the world to him.
Tigger: He sure did!
Eeyore: That's right. He said that. - The policeman pretending to have not heard the 100 Acre wood group speak, despite the cabbie and newspaper seller saying they did.
- When Christopher and Evelyn find Madeline near Winslow Industries after she accidentally loses Christopher's papers, she explains that she went on the entire "expotition" so that she wouldn't have to go to boarding school. A bewildered Christopher then tells her that his new adventure with Pooh and the others have made him see that he was wrong about putting his work over his daughter and that she doesn't have to go to boarding school, with father and daughter sharing a warm embrace for probably the first time in years (and one of the few times in the movie) with Pooh smiling as he watches the whole scene unfold.
- Here is all the scene, if you can take it:
Christopher Robin: (relieved) Madeleine! Thank God we found you! Are you all right?Madeline Robin: (upset) I...lost your papers. I'm so sorry.Christopher Robin: (stunned) Madeline! Darling, that doesn't matter. You're safe. That's all that's important. Not my papers.Madeline Robin: But...your work is so important. I thought that maybe if I brought you your papers, that...you wouldn't send me away and then we could all be together. (shows off half a page she saved) I saved a little bit.Christopher Robin: Sweetheart...I was wrong about work. I was wrong about...everything, and I'm so sorry. I've been a father of very little brain.(Pooh smiles in acknowledgement)Christopher Robin: I lost myself, Maddy. And I almost lost you...my most precious love.(Evelyn comes up with Tigger, Piglet, and Eeyore in her arms, all of them are smiling)Christopher Robin: (begins tearing up) And I don't want you to go away. You don't have to go to boarding school. You can stay here with us, and I'll never let you go.(Christopher hugs Madeline tightly, and she hugs her father back, both crying while smiling.) - It's kind of subtle, but when Christopher storms in at Winslow's, all the employees who were tearfully packing their things in anticipation of losing their jobs immediately look relieved and follow him to the meeting room without question. Ms. Dane even says "Thank goodness you're back!" Christopher's kindness and competence has not gone unnoticed by the employees, and just seeing him return gives them hope that things are going to work out all right. Almost without noticing, he's taken on a similar role at Winslow's as he once did in the Hundred Acre Woods: He's the one everyone admires and trusts to have the answers.
- The last scene with Christopher watching the sunset with Pooh, and those famous words, “Silly old bear,” (pictured above) and it is implied being that visits will be regular once again (presumably whenever they go to the cottage).
- While her patience does start to wear thin with him at times, Evelyn consistently stands by Christopher, even when she feels that he's making poor choices for his own health with how much of a workaholic he is. She immediately goes to him when Madeline is missing, and, while she's clearly (and reasonably) more than a little shocked by the existence of the 100 Acre Wood gang, she accepts their existence within minutes, even carrying Tigger, Piglet, and Eeyore around London for them. By the end of the film, she's casually hanging out with them alongside her husband and daughter, making tea and snacks.
- The credits has a song called "Christopher Robin"
performed by Richard Sherman, which is told from Pooh's perspective about his promise on never forgetting about him alongside how much he misses him after years of separation. The song is very heartfelt and might cause some tears to be shed. Especially when the song is followed up by a piano variation of the "Winnie The Pooh" song during the credits.
"Christopher Robin, look at me"
"Tell me what you see"
"Do you remember how we used to be?"
"You were a special friend of mine"
"We were forever wasting time"
"Keeping busy all day through"
"Just doing nothing with nothing to do"
"Gathering haycorns off the ground"
"Picking up Poohsticks all around"
"Dreaming up something not to do"
"Just being us (soundtrack)/ having fun (credits) being me and you"
"Christopher Robin, can't you see"
"From the very start?"
"We were never meant to be apart"
"Let's be together every day"
"Playing the games we always/used to play"
"Christopher, you will always stay"
"Here in my heart"
"Tell me what you see"
"Do you remember how we used to be?"
"You were a special friend of mine"
"We were forever wasting time"
"Keeping busy all day through"
"Just doing nothing with nothing to do"
"Gathering haycorns off the ground"
"Picking up Poohsticks all around"
"Dreaming up something not to do"
"Just being us (soundtrack)/ having fun (credits) being me and you"
"Christopher Robin, can't you see"
"From the very start?"
"We were never meant to be apart"
"Let's be together every day"
"Playing the games we always/used to play"
"Christopher, you will always stay"
"Here in my heart"
