Chereads / Eternal Simp: Adventures in awkwardness / Chapter 21 - Chapter 21: Medieval Matchmaker Madness

Chapter 21 - Chapter 21: Medieval Matchmaker Madness

Jason Blumbley felt the now-familiar vortex yanking him away from the beach reality show. As the swirling lights and sounds subsided, he found himself standing in the middle of a bustling medieval marketplace. The smell of fresh bread, roasted meat, and livestock filled the air. He looked down to see he was dressed in a tunic and breeches, with a feathered cap perched precariously on his head.

"Seriously, a feathered cap?" Jason muttered, adjusting the ridiculous headgear. "What's next?"

Before he could ponder his situation any further, a stout man with a bushy beard and a booming voice approached him. "Ah, there you are, Jason! Ready to get started with your new job?"

"New job?" Jason asked, bewildered. "What job?"

The man clapped him on the back, nearly knocking him over. "Why, you're the new matchmaker, of course! The villagers are eager to find love, and it's your job to make it happen."

Jason's eyes widened. "Matchmaker? Me? Are you sure?"

The man laughed heartily. "Of course, I'm sure! Now, get to work. The villagers are counting on you."

Jason sighed, feeling a mix of dread and resignation. "Alright, let's see what I can do."

He wandered through the marketplace, trying to figure out how to match people up. His first client was a young woman named Eliza, who was nervously fidgeting with the hem of her dress.

"Hello, Eliza," Jason said, trying to sound confident. "I'm Jason, the new matchmaker. What can I do for you?"

Eliza blushed. "Well, I've had my eye on Thomas, the blacksmith's apprentice, but I don't know how to get his attention."

Jason nodded, feeling a spark of hope. "Alright, Eliza. Let's see if we can come up with a plan."

His first idea was to stage a "chance" encounter. He led Eliza to the blacksmith's shop, where Thomas was hard at work hammering away at a piece of metal. Jason tried to come up with a clever way to introduce them, but his clumsiness struck again.

As he attempted to guide Eliza into the shop, he tripped over a stray horseshoe, sending him sprawling into a pile of hay. Eliza stifled a giggle, and Thomas looked up, curious.

"Uh, hi Thomas," Jason said, brushing hay from his tunic. "This is Eliza. She wanted to meet you."

Thomas smiled, wiping his hands on his apron. "Hello, Eliza. It's nice to meet you."

Eliza blushed and smiled shyly. "Hi, Thomas."

Jason felt a small sense of accomplishment. "There, see? Easy."

But just as he was starting to feel confident, the stout man with the bushy beard appeared again, dragging a reluctant young man by the arm. "Jason! This is George. He's in desperate need of a match. Think you can help him?"

Jason nodded, feeling a bit overwhelmed. "Sure, I'll see what I can do."

He took George aside and asked him about his interests. George's eyes lit up as he talked about his love of poetry and music. Jason decided to introduce him to Mary, the baker's daughter, who was known for her beautiful singing voice.

He led George to the bakery, where Mary was kneading dough. "Mary, this is George. He's a poet and a musician. I thought you two might have a lot in common."

Mary looked up, her eyes sparkling with interest. "Really? I'd love to hear some of your poems, George."

George blushed and nodded. "I'd be honored, Mary."

Jason watched as they began to talk, feeling a sense of satisfaction. "Maybe I'm getting the hang of this."

But his newfound confidence was short-lived. As he continued his matchmaking efforts, his clumsiness and knack for awkward situations turned each attempt into a comedy of errors.

He tried to set up a picnic for Sarah, the tailor's daughter, and William, the carpenter, but accidentally set the blanket on top of an anthill, leading to a hilariously frantic scene as they both tried to escape the angry insects.

He attempted to arrange a romantic boat ride for Alice, the miller's niece, and Robert, the fisherman, only to capsize the boat and send them both splashing into the river.

Despite the mishaps, Jason's earnest efforts and good humor won the villagers over. They began to see his matchmaking as a source of entertainment, and his failures often brought them together in laughter.

One evening, as the villagers gathered around a bonfire to share stories and sing songs, Jason found himself sitting next to Eliza and Thomas, who were now a couple thanks to his awkward introduction.

"Jason, you may be the most accident-prone matchmaker we've ever had," Thomas said, laughing. "But you've got a good heart."

"Thanks, Thomas," Jason replied, feeling a warmth spread through his chest. "I just want everyone to be happy."

Eliza smiled. "And you make us laugh, which is just as important."