The party ventures to a seaside city called “Seaddle.” If your party ever asks about the significance of the name, say something about how the serene sea-breeze and local flora can “addle” one’s brain and make you feel blissfully oblivious to anything else.
The city is clearly a hub for trading as there are a great many shops and businesses in the area; it should feel “urban”.
Since party members usually seek out taverns/inns, if they ask any residents, they will always be pointed to one of the best places in the entire city: “The Place of Pikes.”
Arriving at the inn, they will see the insignia of two crossed pikes (the infantry weapon, not the fish). Once inside, they will enter into a warm and inviting lobby that opens into a larger restaurant/tavern area.
A crowd is gathered around a board on one of the walls. Unlike more RPG-esque tavern boards which may be a place to post quests, this board is entirely devoted to finding love. The board is covered with sketches of local singles looking for romance in the big city and list off “what they’re looking for” and “what they bring to the table.”
As you’re inspecting this board, the barkeep comes over and gives a sigh. He points to one of the papers, clearly aged and curling at the edges, showing the face of a gentle but plain-looking country boy named Beau Woolsworth. His description is very humble and his “looking for” are all admirable qualities: a warm heart, someone who will enjoy his cooking, enjoys walks in nature, a sense of humor, etc.
The barkeep laments that “it’s such a shame that poor Beau is having no luck finding a date. His smiling face has been posted up here for 6 months now.” If your party decides to ask more about him, the barkeep will provide some details:
- Beau is a friendly, cheerful man who comes in here often, although he isn’t one to really imbibe much; his preferred drink is a chilled glass of milk mixed with honey.
- Beau sold his farm and flock of sheep because he was lonely in the countryside and wanted to grow and start a new life for himself here in the big city of Seaddle.
- Beau currently resides in a house beside an abandoned lighthouse on the coast.
The barkeep insists that Beau means well, and he just needs a little help finding and impressing the right person. He eyes your party and comments on how charming and sophisticated (or confident) your party looks. He asks if you would help ‘ol Beau find a date and make a good first impression. If you can play matchmaker, the barkeep will offer your party free room/board for the entire time that you’re staying in Seaddle.
Beau Meets World
If your party agrees, they are directed toward the abandoned lighthouse and Beau’s seaside home. After knocking on the door, Beau will answer and greet his guests with a warm smile and some sweet Southern hospitality. He is wearing a thick wool sweater, which he proudly tells the party that he had sheared from his own sheep and knit himself.
If you tell him why you’re there, he will get very excited and run to grab a letter that arrived in the post just earlier that day.
Reading the letter, Beau tells the party that he has received a letter from someone interested in him, telling him that she’s staying at “The Place of Pikes” for a few days and to drop in tomorrow at seven for dinner.
Beau is very nervous but clearly excited about this prospect. However, according to the letter, his admirer is a “city girl” who seems worldly and knowledgeable. Beau would love a crash course in proper dating etiquette and learn about whatever else the party can help him with (he’s pretty sheltered and innocent, so there’s much to learn).
At this point, assume that Beau’s “charm offensive” level is at 0. Your party needs to decide on various ways to prep Beau, preferably using their individual skills and sharing their particular areas of expertise/backgrounds.
Note that, even when Beau fails to “master” (used loosely here) a skill, he will continue to be optimistic and grateful. Really play up Beau’s character to be endearing and well-intentioned. If your player character does a good job explaining something or describing how they are training Beau/prepping Beau, set the DC to 10. If the player character is vague or doesn’t provide specifics, have Beau wrinkle his brow in an attempt to understand and set the DC to 15.
Here are some ideas and the associated checks.
- A character could give him a quick workout so that his muscles are a little more toned for the date (strength check). It would be best if they can find various equipment around Beau’s small house to help him train.
- A character who comes from a wealthy background could provide Beau with some etiquette knowledge (charisma check).
- A character could lead Beau in learning how to dance and be graceful on his feet (acrobatics check).
- A character who is good at crafting potions could concoct a cologne for Beau to wear tomorrow (nature check).
- A character could walk through a “mock date” situation pretending to be the girl and see how Beau fares in conversation (survival check).
- A sociable character could share with Beau the happenings of politics/juicy gossip in Seaddle and beyond (history check).
For each successful lesson, add +1 to Beau’s charm offense.
If at any point Beau starts to struggle or feel overwhelmed, maybe from 2 failed checks in a row or whatever you as the DM would like, he can start to have a mild panic attack before digging around in a drawer and pulling out a framed photo of all his sheep. He will explain that, although he is happy that he has moved on to something bigger in his life, looking back at his sheep always calms him down (something to note for later).
The next day, the party can grab tables of their own and wait for Beau’s arrival at “The Place of Pikes.” The barkeep can also be informed and keep a watchful eye as well, hoping for a successful date.
When Beau walks in, he is dressed in a nice suit (a little too nice for a casual first date, admittedly, with his buttons askew). This immediately triggers a -1 to his charm offensive score, although your party can artfully try to intervene to help him rebutton his outfit and give him a little last minute pep talk (bringing the charm offensive back up by +1).
Beau will stand awkwardly in the middle of the tavern before being waved over by a pretty woman at one of the tables. She will hold up the flier that shows Beau’s sketch.
While the party watches, they can try to do things to help Beau…
- Walk over and thank Beau for help with something, making him look super helpful and showing that he has many connections in the community (depending on how you play this, complete a “deception check” and potentially earn +1 to charm offensive or -1 if it flops).
- Send a bottle of fancy wine or something to the table as a gift (+1 to charm offensive, no check needed).
- At one point, Beau can start to panic a little. If your party can minor illusion some sheep in the air, or if they drape themselves in white tablecloths and “baa” like sheep, they can calm Beau down from a distance. If they don’t, Beau will calm himself down but take a -1 to charm offensive for his momentary freakout.
At the end of the date, the charm offensive score determines how successful Beau is (and he will come over to the party’s table, either excited or defeated, to tell you). If the charm offensive score ends at a 5+, then Beau gets the second date and is really grateful. Aside from the barkeep holding up his end of the bargain for complimentary room/board, Beau will give you “Beau’s Token of Thanks”: a small white handkerchief with a little sheep embroidered on it. This token gives the holder advantage on all animal-handling checks and gives +1 on persuasion checks (because Beau is so darn lovable!).
If Beau’s date fails, have him still thank the party for all their help. He will insist that he’s feeling sleepy and would like to head home. On his way out the door, have him run into someone: a country girl who has also just recently moved to Seaddle. The two start talking and hit if off immediately (she’s a former dairy farmer) and find themselves a table; Beau looks back at your table, shrugs his shoulder and smiles, and goes off to have a natural and seemingly riveting conversation with this woman. [I really just wanted Beau to have a happy ending to his story regardless]