The original series
- In the episode "Dylan - Sculptor", Dylan gets more and more irritated as more characters keep interrupting him, while he tries to make a clay statue of Dougal. While not entirely upsetting (especially when the clay statue, out of nowhere, comes to life (which isn't unusual considering the show's surreal nature) and announces it's time for bed), it's hard not to feel bad for Dylan, considering how he rarely gets upset (given his usual laidback personality).
- A somewhat similar case occurs in a 1993 French episode which involves Dylan making a portrait of Florence. This episode, however, provides more of a Downer Ending, in which Ermintrude mistakes Dylan's art curtain for a bullfighting cloth and charges at it, ruining the picture. Dylan, of course, is in utter despair, revealing that he was going to display Florence's portrait at an art gallery, while Dougal only finds this funny and jokes that he can display Ermintrude's head instead.
- The episode "Toffee River" has the Train having to stop and let off Dougal and Florence due to a steep bridge ahead. In Thompson's narration, when Dougal and Florence try to object, she has this to say:
Train: (nearly crying) I think you're both being very unreasonable. I'm rather hurt... (sobs) I—I do my best to get you from one place to another and... I—I never complain. (sniffs)
- In Eric Thompson's original narration of the episode with Dougal wearing glasses, Florence asks why he's wearing them. The reason?
Dougal: Isn't it obvious? None of us are getting any younger... even the keen eye of the watchful dog begins to need an artificial aid or two...
Florence: But Dougal—
Dougal: No, no, please. Don't interrupt. I don't wear them for pleasure, you know.
Florence: But Dougal, I—
Dougal: Please, please, don't try to be kind. I know what you're thinking. "Poor old thing, he's past it." That's what you're thinking...
Florence: I'm thinking no such thing. If you'd just let me explain...
Dougal: Explain? Explain? Oh, I know what you will explain. You will explain that your friend is still your friend, even though he was growing old and... grey and... useless. (sobs)
Florence: Dougal, I think you're getting rather maudlin.
- The episode "Speed Limit" has Dougal briefly in tears when he seems to have lost Brian, after giving him a ride on his back.
- A small one, but at the end of "Watch the Birdie", when the birdie they need for the camera flies away, Mr. Rusty has this line:
Mr. Rusty: Oh, it's flown away. Now there won't be any photograph and prosperity will forget we ever existed. Sic Transit Gloria Mundi [Latin for So passes the glory of the world]...
Brian: I may cry.
- Unfortunately, this is a Truth in Television, as several TV shows and movies, etc. tend to be forgotten within long periods of time (especially the more obscure ones that are fondly remembered by only a few or many depending on the show's popularity).
- To push it further, this was the last new episode to air in the UK before the three-year Series Hiatus from 1971-1974. (Granted, the show was popular enough to still air in reruns during that period, and 1972 saw the release of the film Dougal and the Blue Cat in English, but at the time, it was uncertain whether or not the series would return.)
- Nigel Planer's re-narration of the 1971 episode, "Business Trip" (a.k.a. "Holidays") is rather melancholy, involving a Moving Experience plot with Mr. Rusty, Florence, and Dougal thinking that Brian is leaving the Garden forever. There's even soft piano music playing in the background during the entire episode. While it's unstated where Brian is actually going, it's eventually revealed at the end of the episode that he's only leaving for the weekend.
Zebedee: (sibilantly) Sometimes, all of a sudden, someone sets forth, leaving everyone somehow suddenly sadder.
- Ermintrude getting upset over gaining weight in "Ermintrude's Slimming Campaign" (or Le Régime) and "Dougal's Massage Machine" (or La Machine à maigrir).
- In UK book/annual adaptations of the original series, whenever Ermintrude cries.
- The 1971 annual dedicated to Dougal features a story ("Ermintrude's Problem") where Ermintrude is weeping buckets and Florence and Basil take Dougal to talk with her (it's even stated that the cow looks up to him). However, Ermintrude is so upset (to the point where even Dougal feels sorry for her) that she's unable to say what's troubling her. Dougal suggests she should tell her problem to a nearby tree, where it's revealed that she's upset about being too big to ride on the Train for her birthday. Thankfully, the friends make her a little carriage for her to fit and ride in.
Dougal and the Blue Cat
"Oh, tell us it's a game, Buxton..."
- To beloved fans of the show, something about seeing each your favorite characters being hastily captured and locked up in a dungeon and taken from their cozy garden home just feels so wrong.
- Florence screaming for help as she's being captured (in the original French version, she calls for Dougal, while in the English dub, she calls for Zebedee who has already been captured).
- Dylan, aware of the situation, seems bizarrely casual about it at first, and asks for a bit of silence so he can nap. If that weren't enough, in the original French version, he even admits that he doesn't mind being kidnapped and Buxton has this to say:
Buxton: (French version) It will be your last sleep, my dear Flappy. This cave will be your grave.
- Florence's sad song. The entire song is just DEPRESSING, especially the chorus lyrics.
Florence: (singing) Shall we ever see the sun again? Shall we ever feel the rain again? Shall we ever play our games again? Or will the games we play end here? (sobs) Oh, Dougal... where are you? I'm sorry, Dougal... I'm sorry. It's all my fault. But I thought everything was all right... like it usually is. It's all my fault...
- Certainly not helped that everyone else cried along with her. Especially if you consider the immense guilt that Florence, Dylan, Brian, and Ermintrude are feeling, given how they didn't believe Dougal when he warned them about Buxton.
- It's also the first time we see Florence and Brian with visible frowns. Seeing the two most cheerful characters in a mournful state is truly heartbreaking.
- The lyrics of the original French version, which has her singing about missing Dougal and holding onto hope for his return, are arguably sadder and deeper.
- To top it off, in the French version, this all happens on her birthday (even though it's only mentioned once). A Birthday, Not a Break indeed...
- Brian's Disney Death after the snail goes back to retrieve Zebedee's magic moustache from the factory, just before it collapses. Dougal tearfully even admits that Brian really was his best friend. It's also hard not to feel bad for Buxton, as he tearfully wallows in guilt, after having been stripped from his reign of power. Even Brian, who shows up alive, is moved to tears by this, and convinces the gang to forgive him.
The 2005 film
- Zebedee's Disney Death.
- When the gang get the first diamond in the volcano, they see a vision of Florence and the children still trapped in the frozen roundabout through the diamond. When Dougal tries to speak to her, the vision fades away from the diamond, leaving Dougal and the others depressed, before Zeebad suddenly arrives to ruin the moment to take the diamond and the map from them.
- The gang trudging through a snowstorm on their way back to the village and almost losing hope.
- Following Dougal's nightmare about Florence, he instantly wakes up and screams out her name in distress.
- Florence's Disney Death near the end of the movie with Dougal begging her to wake up.
Dougal: (UK dub) Florence, can you hear me? Please wake up! Please wake up. Don't leave me! This world means nothing without you. / (USA dub) Florence, please wake up! Don't leave me like this. I ran across the entire world for you. I don't know what I would do if I can't see your smile again...
Dylan: Sorry, old buddy...
Dougal: No, it can't... she can't! Florence! (sobs) (UK dub) My lovely Florence! / (USA dub) My best friend, Florence...
The CGI series
- In "The Wishing Tree", Dougal unwittingly uses his third wish to make everyone, who keeps bothering him because of his second wish, to go away. When Dougal looks around the gardens, it turns out that his friends are completely gone and nowhere in sight. While poor Dougal learns on how selfish he was for making those wishes, it's hard not to feel bad for him when he regrets making his third wish when he begs the titular wishing tree for his friends back.
- In "The Party", because of everyone, including Dougal, are avoiding Florence when she tries to ask them to help her fix her fence, this made her feel very upset and even so hurt when she finds Dougal hiding from her in a rubbish bin. This was prompts her to pack her suitcase and leave to go and visit some friends alone. Everyone begins to feel bad when they heard from the news from Zebedee, who had witnessed this, and they tried to make it up to her as well as persuade her to come back, but she crossly refuses. When Dougal tries to convince his beloved friend and owner to come home, Florence refuses as she is still not very happy with him for constantly avoiding her earlier and doesn't even bother turning around when Dougal lets out a little bit of the surprise to her.
Dougal: Come along now, Florence, stop all this silly sulking. Let's go home and have our dinner.
Florence: (sternly) I am not sulking, Dougal! And I am certainly not going back home just to cook your dinner!
Dougal: But I can't cook!
Florence: Then you'll have to learn how to!
Dougal: But, if it's, if it's about this morning, I really was busy.
Florence: (upset) You weren't busy, Dougal, you just didn't want to help me mend my fence!
(She angrily goes around Dougal.)
Dougal: I know it may have looked like that, Florence, but I was, in fact, preparing a big surprise for you!
Florence: (without stopping or turning around) You can't expect me to believe that!
Dougal: Come back and see for yourself!
Florence: No, Dougal! I'm going to see a friend!
Dougal: (sighs sadly) She won't come back.
- Afterwards, Florence begins to feel bad and remorseful when she was cross with everyone and her voice sounds so distraught when she talks to herself about it. Fortunately, Zebedee secretly lured her back to her house by diverting the path she's walking on and this tearjerker moment will turn into a heartwarming moment where they manage to pull the surprise party off for her, but still, poor Florence...
Florence: (sadly) Oh dear, I hope Dougal isn't hungry. Poor Brian, he looked quite upset when I was cross with him. And Dylan, Dylan can never mend a broken guitar string. (Later, when she is almost at her house where everyone is waiting.) Poor Ermintrude, I hope I didn't offend her. And I should never said no to dear Mr. Rusty.
- This moment in "Rockstar Dylan" when Dougal leaves Dylan after seeing how rude and arrogant he has become when trying to be a rockstar, poor Dylan sits alone on the steps of the bandstand, feeling very depressed after realising how rude and arrogant he was and plays a sad tune on his guitar.
- In "Ermintrude Gets A Fright", Florence is depressed that the pair of mice she has found in her strawberry patch had scampered due to Ermintrude accidentally scaring them off when she screamed in fright. Whilst everyone, except Ermintrude who feels bad after ruining the strawberry patch, Florence just sits there on the doorstep of her house, still devastated with Dougal comforting her.
- Florence crying in "Florence's Squeaky Toys" when the toys she delivered to Basil and Coral go missing (after Mr. Grimsdale accidentally mixes the deliveries due to losing his glasses), leaving her devastated that she will have nothing to give for them. Fortunately, Dougal (who unknowingly hid the toys out of annoyance), with Mr. Rusty's help, managed to find the toys.
- Dylan getting disheartened in "Dylan's Big Gig", when Dougal accidentally wrecks the sound and lighting systems for a big show the former was going play that night. He even plays a sad tune to himself on his guitar, while the others try to find a solution. Fortunately, things work out, but still, poor Dylan...
Dylan: (singing, near tears) I've got the big gig disaster blues... (sobs)
- Dylan becomes a Woobie again in a later episode ("Who's Taken the Moon?"), when he gets upset that the full moon he likes to serenade seems to have been "stolen", and is unaware of the moon cycle, which he has never been awake long enough to see.
- Brian's devastation in "Interior Des-Aster" after Ermintrude, riding Mr. Grimsdale's bike, accidentally crashes into the snail's house, leaving it wrecked.
You know, I'm not one to make a drama out of a crisis, (tearing up)
but in this case, I think I shall make an exception! (bursts into tears)
- In "No More Magic, Zebedee", Zebedee gets really devastated and upset that Mr. Rusty had taken out the magic gasket from the Magic Roundabout to try and teach him a lesson for taking away their favourite things (which was all because of Zebedee's misunderstanding) and begins to leave the Enchanted Gardens with a bindle stick as everyone looks on, now feeling bad for what they did to him. Florence even feels sorry for Zebedee because she was the only one who doesn't believe that he should receive that kind of treatment from everyone as she was against Mr. Rusty's idea at the beginning. Fortunately, Mr. Rusty replaces the magic gasket back in and restores Zebedee's powers back.