“Save the princess from herself.” That thought, this seed of an idea, has been knocking around my head for almost a year, but I could never get past the premise. But with National Princess Day today, I knew I had to release something princess-related. So, after some intellectual racketball, I come up with this short little dungeon adventure that takes the classic fairytale trope of a princess in a tower and gives a farcical twist. Hope you enjoy

The Princess and Her Dragon

An adventure for 4 to 5 players of level 2

A Fairytale Tableau

The players are traveling when they stumble across a fork in the road with a sign saying, “Damseled Princess in Tower: half a mile,” pointing down the fork. If the players decided to investigate, they discovered the following scene. Read the following aloud.

Just beyond the woods is a scene that is straight out of a book of fairy tales. The road ends in a sun-dappled meadow of wild grasses and flowers with a meandering babbling brook at one edge. A single tower of white stone, five stories high with a conical red roof bedecked in ivy, sits in the middle of the meadow. Turrets with their own conical hats buttress the central tower. At the top, you can see a balcony of the same stone as the tower, and you can just make out a single figure in a pink gown on the balcony.

The woodlands: The woodlands are deep and green, as if plucked from a fairy tale like the tower.

However, the woods hide a dark secret. If the players decide to poke around in the forest, they discover skeletons, all in fine clothes and what once was shining armor. Some are crushed, some burned, and some ripped apart. However, most seem to have been hung or clutch daggers through their chests as if they had stabbed themselves.

There are only fragments of notes on the apparent suicides. All references are failing at one of the tests in the tower. Among the fragments are.

“She called me ugly — me, ugly?”
“Who talks about magic theory at the dinner table?”
“She called me an oaf for trying not to stab my own foot…”

Treasure: Among the remains, the party can recover assorted jewelry, coins, and trinkets worth 200 gp in total — grim relics of those who once sought to win the princess’s favor.

Dragon “Attack”

As the players enter the meadow, a Young Red Dragon( see stat block at the end of the post) swoops down to attack, taunting that they will never free the princess. However, something seems wrong; the dragon does not seem enthusiastic about attacking the players, its attacks seem half-hearted, and its taunts seem forced. A player can make a DC 14 insight check as a bonus action to determine that the dragon does not want to fight the players.

When the dragon reaches half hit points, she recoils from the party and shouts time out time out repeatedly until the players stop attacking. She sighs like she’s done this a million times before and says they have passed the Test of Galantry and earned the right to “save” her “mama”, Princess Eleniel of House Faevane. She then half heartedly walks towards the tower, shape-changing into a wyrmling when she gets to the door at the tower’s base.

The tower of the Princess

Once upon a time, this was the tower of an archmage who was best known for his attempts to capture sunlight in oranges for later reuse. Princess Eleniel and Scarlet have long since had the tower refurbished and transformed into a gauntlet for Princess Eleniel’s suitors to run.

Features

Ceilings: The ceilings are 15 feet high unless specified otherwise.

Light: The rooms are lit with sconces and chandeliers, with the continual light spell cast upon them.

Windows. The windows are all 4 feet wide by 5 feet tall and open outward. They are all unlatched.

Ivy. The ivy growing outside the tower is strong enough to support the weight of a full-grown man and grows all the way up to the top of the tower.

Doors: All the doors are indestructible and lack keyholes

Scarlet’s Room

You step through the entrance into a small, cozy reception room. There is a scattering of red velvet armchairs around a fireplace. A bright red carpet leads across the stone floor to a flight of stairs leading upward. A large pet bed is by the fireplace, with the wyrmling from before curled up inside. The wyrmling is making big, longing eyes at a painting of a princess across the room. There is a door to another room besides the stairs.

Once upon a time, Scarlet would brief the potential suitors on the game’s rules in this well-appointed parlor. Now it serves as her lair where she pines after her Mama.

Wyrmling. The wyrmling is curled up on a luxurious, large pet bed, “Scarlet” emblazoned in golden stitching. She is staring at the painting with longing eyes and whimpering softly.

If the players try to engage her in conversation, the wyrmling sighs and says they have already passed the first part of the game; they have earned the right to climb the tower, not that they could pass the other tests, Mama never gave any of the suitors who tried before a chance. She will not say anything more until the players realize the connection between her and the princess.
If asked, she tells the player characters that her name is Scarlet, and she was Princess Eleniel’s most beloved pet.
- Scarlet speaks with a slight lisp on her Rs in this form.
- Scarlet comes off as an overgrown mama’s girl who would love to be the little dragon in the painting again and play with her mama like she did before she got too big.
If asked why she assumed this form, Scarlet replies that she does not want to grow up; she wants to stay Mama’s baby dragon pet.
If they ask why she attacked them, she tells them it’s her role in the game: to serve as the dragon guarding the princess.
If the players ask Scarlet why she is not with her Mama, she starts to cry. She explains through tears that Eleniel has forgotten she is a grown-up dragon and, in her madness, replaced her with a stuffed replica she had made when Scarlet got too big to sit on her lap. She thinks it’s alive, and she talks to it like she used to speak to her.
The Game. If they ask about the game, Scarlet will explain everything.
- Princess Eleniel locked herself in the tower because she was bored and found traditional courting tedious. She figured that playing out a fairytale roleplay would be a good way to sift through suitors for a proper Prince Charming.
- The floors above have three more trials meant to test potential suitors. Each one tests for one of the traits Eleniel thought would make a good Prince Charming. The mock fight against Scarlet was the first trial.
- However, Eleniel’s definition of what makes a prince charming is precise and frankly a little unrealistic; over the last few years, she has turned down hundreds of potential suitors.
- Scarlet shudders when she tells the next part. Eleniel has gone funny in the head; she thinks she is being held against her will by Scarlet, that Scarlet killed her parents, and her only hope is that Prince Charming will come and save her.
Scarlet’s Quest. If the players listen to the story, Scarlet will ask them to free her mama from her prison of self-delusion. She will offer to accompany them and give hints on overcoming the trials.
- Alternatively, she would be satisfied if they could sneak herself in wyrmling form into Eleniel’s apartment at the top of the tower and replace the stuffed scarlet with her.

Armchairs. The chairs are red velvet and well-worn, but they look incredibly soft.

Anyone who takes a short rest while sitting in the chair gains an additional 1d4 hit points per short rest

Painting. The painting is of an elf girl with a fair face and blond hair, approximately age 7, in a pink princess dress, bedecked in lace, layers of peticoats, and a gold tiara. A familiar-looking wyrmling is sitting in her lap.

The wyrmling is the same as the one on the pet bed across the room
At the bottom of the painting is a brass plate that states that the subjects are Princess Eleniel and Scarlet the Wyrmling

Door. The door leads to a small closet filled with canned dragon food and cleaning supplies.

If the players search the closet thoroughly, they find a stash of healing potions. If asked, Scarlet lets them help themselves to the potions.

Stairs up: The stairs lead to the next floor and the first trial

The Trial Of Charm

At the top of the stairs is a large, long, elegant dining room. A single high-backed chair sits at the head of a table set for twenty. The walls are lined with paintings of elven nobles in lavish outfits. There is a door opposite the stairs and another door leading to your left.

Scarlet’s commentary. If the players brought Scarlet along, she would have the following clues for the trial:

To start the trial, you only need to sit in the chair; several illusions of noblewomen and noblemen will appear for a dinner party and engage the subject in the chair in conversation. The door to the next level will unlock if the subject can engage in the discussion with charm and grace, despite the often absurdity of the topics of conversation.
Before you ask, yes, the food is edible.
The person sitting in the chair cannot stand until the test ends.
The magic for the trials is pretty dumb. It assumes that only one person is taking the test at a time and completely ignores everybody else in the room. However, the person in the chair must engage in the conversation.

The table and chair. The trial begins when a person sits in the chair at the head of a table.

The Trial. As soon as one of the player characters sits in the chair, illusory nobles, mostly pretty young noblewomen, emerge from the painting and sit at the table.

Once all the participants are seated, unseen servants lay out a luxurious five-course meal. Once everything is set, the illusory noble turns to the player character seated among them. One by one, they engage the player in following conversations. Communicate to your players that they do not need to make checks to pass the trial, and can succeed through the use of roleplay alone.
- The first conversation: One noblewoman engages the seated player in small talk. If the players can engage in charming small talk in character or succeed on a DC 15 persuasion or deception check they pass.
- The second conversation: One of the noblewomen asks the player to recount their adventures. The player must tell the assembled nobles of their greatest adventure with a level of energy and detail to excite them, or pass a DC 18 performance check
- The third conversation: One of the noblemen discusses the following moral dilemma: If you are forced to choose between saving the child of a pauper and a wealthy king, who would you save and why? The players must give a well-thought-out argument for their choice or succeed on a DC 21 Wisdom check
- The fourth conversation: One of the noblemen engages the seated player in a complex discussion about magical theory. The players must contribute to the conversation with the confidence of someone who is familiar with the topic (even if they are entirely ignorant of the subject matter) or they must succeed on an Arcane Check DC 22 or a Deception Check 18.
The players can succeed by making one of the suggested skill checks or through the suggested roleplay. The illusions cannot perceive the players standing around the table, so the seated player does not need to be the one to make the skill checks and can have the answers whispered into their ear.
The player aims to impress the nobles with their wit and charm. If they successfully impress the guests, the ladies swoon, and the men applaud. When they fail, they recoil in revulsion.
If the seated player can impress in 3 out of 4 conversations, the door unlocks upward. If they fail to impress, the nobles recoil in revulsion and call the player character a dullard. The seated character is then spat out of the chair onto the floor, and the door remains unlocked.
Each player can only attempt the trial once

The Door to the left: The door leads to a small but fully stocked kitchen manned by unseen servants.

The kitchen has enough food to feed 10 people for 40 days. Scarlet admits she has no clue where the food comes from
A search of the room reveals a dumbwaiter that goes upward. Scarlet is pretty sure it goes straight to the Princess’s chambers.

The door in front. The door is sealed using magic until the trial is complete.

Paintings: The paintings are well done, but faded and incredibly dusty.

They depict various elven noblemen and women between the ages of 17 to 25 in luxurious clothing

Treasure: The paintings are worth 500gp to the right dealer

The trial of Grace

At the top of the stairs is a large ballroom with low, atmospheric lights. A waltz is played in the background. A single statue of a princess stands in the middle of the room, humming to herself in time to the waltz as if waiting for a dance partner. There is a door on the far side of the room.

Scarlet’s commentary. If the players brought Scarlet along, she would have the following clues for the trial:

This is a test of grace; you only have to dance with the statue until the song’s end.
Be careful, the floor is covered with caltrops, china, and other nasty surprises.
The door will open if you can complete the dance without messing up or breaking anything.
Scarlet is pretty sure the magic of the trial does not track where the obstacles are on the floor or if they are on the floor at all.
She sighs and says that you see what she means when her mama has unrealistic notions of what constitutes a perfect Prince Charming

The Trial: The trial begins when one of the players steps out onto the dance floor and takes the statue’s hands. The music swells into a waltz, and the statue takes the lead.

The floor is covered with caltrops, grease puddles, teacups, and other things that would cause damage or cause the player to stumble if stepped upon. The player dancing must make a DC 22 Dexterity check, or they will stumble and mess up the dance.
- If the dancing player screws up the dance, the music stops, and the statue gives him or her a good shove in disgust and sneers at them. If the player tries to approach the statue again, she gives them a good slap across the face.
- If they can keep up with the statute, she releases them with a giggle and curtsies politely.
The players can clean the floor before attempting the trial using the brooms and cleaning equipment in the reception room’s closet. If they do, the dexterity check is reduced to DC 5 to keep up with the statue’s moves.

Door: The door remains closed and locked until the trial is completed

The trial of Handsomeness

The stairs deposit you into a narrow hall that ends with a curtain. The walls are papered with floral patterns and are lined with portraits of handsome men, including a painting of Fredrick Von Mountainheart. On the sides of the hall, doors lead to bedrooms and a large bathroom.

Scarlets commentary. The players brought Scarlet along; she would have the following clues for the trial.

This is the last and hardest trial; you must prove your handsomeness.
There is a door behind the curtain with a carving of Eleniel’s face. When you pull the cord to open the curtain, the eyes on the carving will open. The carving judges the suitor’s appearance, and the door will open if it finds their appearance handsome, as per Eleniel’s preferences.
However, Eleniel has impossibly high standards for handsomeness. The players will inevitably fail if they rely on their good looks as they are now.
Like the other enchantments in the castle, Scarlet does not think the door is smart; it could be tricked using illusions or paintings.
If asked to describe what Eleniel will consider handsome, she says the men in the paintings on the wall give a good idea of what attractiveness is to Eleniel.
Also, Scarlet will recount that, like most young women, she would daydream of being Fredrick Von Mountainheart’s beloved practically every day.

Trial: The trial begins when the players pull the code to open the curtain. The carving of Eleniel on the door will open its eyes and judge the suitor’s looks based upon what it sees.

If the door is charmed by what she sees, she will swoon, and the door will open.
If they fail, it screams in revulsion, the offending creature is teleported back to the tower’s entrance, and they are overcome with the feeling that they have failed.
The players must trick the carved Eleniel into believing a handsome man is standing before her.
- Scarlet’s belief that the magic enchanting the door is not very smart is correct. The door will open if the players produce the illusion of a handsome prince, use magical disguises, or hold up one of the paintings on the wall to the face in the door.
- It will not open if they attempt the trial without disguises and a significant amount of makeup.

Bedrooms: The bedrooms were once guest rooms for the previous owners’ guests.

The rooms are covered in thick dust, but the furniture is in good condition and quality.

Each room contains a bed, two nightstands, a wardrobe, an armchair, and a dressing mirror.

The wardrobes in each room are surprisingly well stocked with various articles of fine, noble clothing. Scarlet believes they are items left by previous suitors.
In one of the rooms is a hat of disguise, a set of artists’ tools, and a sketchbook.

Bathroom: The bathroom is an expanse of white marble with a sink, toilet, cabinet, and a large stone tub.

All the fittings are in good condition and fully functional
The cabinet is well stocked with soaps, oils, cosmetics, and lotions
- Among the bottles is a tin of cosmetic clay, one application. As an action, a player can make a DC 17Dex check to sculpt the clay onto their own or another’s face to change their features.

Eleniel Suite

Entered via the stairs

You step from the stairs into an overwhelmingly pink and girly room. Everything is colored pink and covered with frills. The princess-style bed is overflowing with stuffed toys, including a life-sized red dragon wyrmling. Sitting at a chaise lounge is a 25-year-old woman dressed in the frilliest pink dress you have seen, with a messy tangle of blond hair that reaches to the floor and tiara. The moment her eyes meet yours, she faints.

Entered via the balcony

You stand at the threshold of a suite that obviously belongs to a princess. Everything is pink, frilly, and girly. On the bed, there is a mountain of stuffed toys, including a life-sized red dragon wyrmling. Lying among the pile is a woman in a pink ball gown with long, tangled blond hair. She is talking to the Red dragon stuffed toy and seems to think it is responding to her.

Entered via the Dumbwaiter

You exit the dumbwaiter into a dining parlor with a fine dining table set for one. You can see a young woman talking to herself in a larger space beyond.

Eleniel. Eleniel uses the noble stat block.

Eleniel’s delusion is specific, not total: she genuinely believes she is trapped by a dragon that the stuffed Red Dragon Wrymling on her bed is her precious pet Scarlet, but she can still reason, converse, and make emotional connections. Her sense of reality is filtered through fairytale logic.
- She speaks eloquently and politely, as a noble would.
- She misinterprets everything in fairytale terms.
- Her delusion counts as a form of indefinite madness. Only a greater restoration spell or similar magic can end the effect
  - Removing the delusion does not change her personality and makes her even more devoted to her prince charming.
She will automatically assume that anyone who appears in her suite is here to save her from the evil dragon.
- The first thing she will ask is, “Oh heavens! Have you slain the wicked dragon? Tell me she’s gone, the dreadful beast.” If the players do not answer, she will go to the balcony to confirm if the dragon is gone.
She has long forgotten about choosing the perfect Prince Charming or the trials she devised. If confronted by a group of people, she will declare the Player character closest to the traditional depiction of Prince Charming as her prince and savior.
- She will insist on an immediate wedding for her prince and will not bear to be more than a few steps from his side at all times.

Stuffed Scarlet: The stuffed toy perfectly recreates Scarlet in her wyrmling form.

In her madness, Eleniel thinks the toy is the real Scarlet and talks to it like it is her precious pet.
However, she cannot distinguish between the stuffed one and Scarlet’s wyrmling form.
- When Scarlet says anything, Eleniel will immediately rush over to her and start cuddling her precious pet, the long-forgotten stuffed toy forgotten. Scarlet nearly breaks down in tears as she basks in the comfort of her mother’s touch — after years apart, this is the reunion she’s dreamed of, even if her mother doesn’t truly see her yet

Conclusion

Eleniel insists her “Prince” carry her down the stairs in his arms and bears him no argument otherwise. She directs the party to make haste to her family’s castle, which, much to everyone’s surprise, lies only a few miles down the very road they were already traveling.

There, the party is greeted by the astonished and overjoyed King and Queen Faevane, who are both relieved to see their long-lost daughter and quietly horrified by the state of her mind. They immediately summon a healer to restore their daughter’s senses.

In gratitude for rescuing the princess, the royal couple knights the party and grants the newly betrothed “Prince” ownership of the tower and the surrounding lands. The rest of the group is rewarded with 600 gp, and preparations for the wedding begin at once.

When the healer’s spell of greater restoration lifts the fog from Eleniel’s mind, the results are… mixed. Though her delusions fade, her affection for her chosen prince only intensifies. She now adores him with unshakable devotion, seeing in him every virtue of storybook romance. She refuses to be apart from him for more than a few minutes, accompanying the party on all their adventures — tiara, gowns, and all — and greeting every danger with fluttering excitement and unhelpful commentary.

Scarlet, meanwhile, is overjoyed to have her mama back to normal. She remains in her wyrmling form, determined to stay her mother’s precious pet. Never again is she replaced by a stuffed toy, and the two live happily ever after in their own strange, fairy-tale way.

Scarlet the Red

Small Dragon (Chromatic), Chaotic Neutral

Armor Class 15
Hit Points 37 (5d8 + 15)
Speed 30 ft., climb 20 ft., fly 50 ft.

STR	DEX	CON	INT	WIS	CHA
15 (+2)	14 (+2)	16 (+3)	10 (+0)	11 (+0)	14 (+2)

Saving Throws Dex +4, Con +5
Skills Perception +4, Stealth +4
Damage Immunities fire
Senses blindsight 10 ft., darkvision 60 ft., passive Perception 14
Languages Common, Draconic (understands but speaks only in baby-talk growls)
Challenge 2 (450 XP) • PB +2

Innate Spellcasting (Shapechange)

Scarlet’s innate spellcasting ability is Charisma (spell save DC 12).
She can cast the following spell once per long rest without material components:

Shapechange (Limited Form).
Scarlet can assume the form of a Red Dragon Wyrmling or a Small humanoid child.
- Her statistics remain the same except her size.
- She cannot use Fire Breath while transformed.
- Dropping to 0 hit points ends the effect.

Actions

Bite

Melee Weapon Attack: +4 to hit, reach 5 ft., one target.
Hit: 7 (1d10 + 2) piercing damage plus 3 (1d6) fire damage.

Tail Slap

Melee Weapon Attack: +4 to hit, reach 5 ft., one target.
Hit: 6 (1d8 + 2) bludgeoning damage.

Fire Breath (Recharge 6)

Scarlet exhales fire in a 15-foot cone.
Creatures must make a DC 13 Dexterity saving throw, taking 21 (6d6) fire damage on a failure, or half damage on success.