It's depressing being a Lady!! character.
The Woobie
Anime
- Sarah. She's an Ill Girl and only had one friend in her whole life before Lynn showed up, being Arthur. George neglects her because of his workload leading her to be be bitter. As soon as Lynn shows up, she unintentionally takes away everyone's attention from her, making Sarah all the more insecure. She starts fearing that even Arthur likes Lynn more than her. Then, when the Marble Mansion is sold off, Sarah is allowed to reside at Duke Warbawn's castle...who demeans her for not being a "proper heir" because of her weak consitution and says that George should get married to Madeleine "to produce a proper heir". At one point, Sarah's health is so bad she has to be taken to a sanitorium.
- Lynn. Her mother is killed when she's a child, and she finds out when Madeleine crudely tells it to her face. Sarah rejects her because she's still coping with her own trauma of being neglected. At home, George is rarely present, and Madeleine, Mary and Thomas all terrorize her in different ways - Madeleine by being the worst Wicked Stepmother she can be, Mary by finding out what hurts Lynn mentally and using it to harm her, and Thomas by physically harming and attacking her and Edward. Thomas and Mary make Lynn cry moments after meeting them. At school, Lynn is hated because she's The Ace and a star student, making the other students that want to win the Lady's Crest jealous - as a result Vivian is always mean to her and Mary tries to blackmail her into staying out, by holding her familial debt over her head.
- Suheir Fahad, Lynn's Arabic voice actress, even admitted to crying many times when voicing her, bemoaning how she was always full of empathy no matter her suffering.
- Misuzu was abandoned by her own parents for marrying George, never accepted by George's family, and when she finally tries to reunite with her husband, she's killed off in a car accident. The scene where she stares in shock at the oncoming truck is absolutely chilling.
- In the first series, there's a maid named Jill who, after witnessing Thomas and Mary heap mountains of abuse on Lynn, finally snaps and slaps Thomas. While it's understandable why Madeleine would be upset (since Thomas is a child and Jill is much older), it doesn't take away from the fact that Thomas repeatedly bullied Lynn, and in that specific instance, implied it was her fault Misuzu died in a car crash.
- Tom the Gardener. He had been a surrogate father figure to Lynn in George's absence, but because he found evidence that incriminated Thomas in Edward's injury, Madeleine fired him. Tom felt saddened at having to leave Lynn, as she made his days at work a little bit brighter. Lynn sorely misses him and it plays a role in her choice to run away.
- King the Squirrel endures being thrown around, yelled at and nearly run over due to Sophie's indifference. He's even rejected by Lynn's cats when he tries to befriend them for being Sophie's pet. Thankfully, Sophie has a Jerkass Realization and changes her ways to be more kind to him.
- Andrews watched his mother die when he was a little filly. Because he had impeccable riding skills, he was taken in by Vivian Spencer...who proceeded to whip and abuse him to keep him loyal and dedicated to her. And when Vivian takes a liking to another horse, she orders that Andrew be put to sleep.
- Arthur in the episode where Mary strongarms him into being her date to the ball, making Lynn cry. Arthur is on the verge of tears too, but keeps silent because of the blackmail Mary has on him. And to upp the ante, Edward mistakes the situation as him genuinely liking Mary and socks him. Arthur's sadness takes another meaning when you remember that his true love is Sarah, and she can't go to the ball.
- Vivian Spencer spent her entire life working towards a dream of being a master equestrian, only for Mary to destroy everything out of her own bitterness. This is after she had been nothing but generous to Mary. Having lost the ability to walk, she gave Lynn her blessing to win the Lady's Crest, while accepting that she can no longer ride.
Manga
- Patricia Rogers, who has been constantly stalked by Thomas for years. Nothing she says convinces him to stay away because of his Entitled to Have You attitude. It takes Thomas being beaten up by one of the Ichijuuins for him to learn his lesson and back off.
- Charles Russell. His father George dies when he's a few months old. Then, the Russell-Waverly family begin losing their wealth as the costs of the Viscount estate are too much for Madeleine. Madeleine frequently yells at him to vent her frustration, berating him for things as small as asking for toys.
- Though they admit they weren't perfect, Misuzu's own parents are also this. Misuzu refused to speak to them for years because they never accepted George. It's mentioned that the two got married at a church where they were the only attendees. While George at least had a wealthy family and supportive friends, Misuzu had none of that as she raised Lynn alone as a single mother for five years. After she died, her parents felt terrible for how they treated her and tried their best to shower Lynn with love and attention to make up for it. Misuzu's mother even tears up seeing the wedding dress she wore years ago.
Jerkass Woobie
Anime
- Mary's cat Prince. He lives in fear of Thomas attacking him with his BB gun. Mary was initially protective to him, but started being abusive to him as well. Of course, Prince was mean to Lynn a few times (like purposely muddying her dress) but he's a cat, it's not like he knows any better (though some episodes imply he has human-level intelligence and understands humans). Lynn takes a shine to him and adopts him, and he becomes a nicer kitty.
- Sophie from the second series is initially quite unlikeable as she always tries to wreck Lynn's already-unpopular reputation in front of Isabelle, but becomes increasingly sympathetic as the story goes on. When Sophie's alone, she's always crying because of her mother's abuse.
Manga
- Baron Gruffald has long accepted that he can't race like he used to, because of a Career-Ending Injury when he was young. No wonder he's such as stoic Jerkass all the time.
