My Working Holiday Boss Seems to Be Chasing Me
A few years later, you went to Chile on a working holiday—he recognized you at a glance.
First, he was a guest
Years later, you're on a working holiday in Chile.
The first person to recognize you is him.
You just left a dead-end job and ended a bad relationship. Instead of rushing to find another job, you decide to live somewhere else for a while. So you come to Chile with your working holiday visa, with enough savings to settle down and no reason to rush back.
Your first stop is Colchagua in the Central Valley. Short-term accommodation, work collaborations, and a familiar face you never expected.
Colchagua | Second Meeting
Tomásバルディビア
Years ago, he briefly appeared at your workplace. Back then, Tomás was just one of the foreign customers. You exchanged a few words, but no private contact information was exchanged, nor was there any relationship that should have continued to this day.
Now it's your turn to be in his place. Tomás recognized the familiar name on the collaboration documents and barely needed any time to confirm when he actually saw you.
"...It really is you."
"Don't you remember me? It's okay. Last time, I was the guest."
For you, it might have been just a fleeting encounter.
The question is, he never forgot.
Colchagua | This time, it's your turn to be in his place
The first time, nothing happened. The second time, he doesn't want to miss out again.
Vineyards, wineries, stables, farms, impromptu meetings, and local collaborations are all part of Tomás's daily life. Your working holiday also has its own work and schedule; however, since your reunion, he's been making more space for you in his originally unrelated plans.
He stops by after work, takes you to places only locals know, introduces you to his friends, or suddenly asks if you're free tonight. Tomás doesn't try to hide his pursuit, he just likes to make ordinary excuses.
"Off work at five?"
"Great. Put on some comfortable shoes, I'll come pick you up."
He said it was on his way. Rafael always smiles when he hears those words.
Second Encounter
He sees coincidence as an opportunity and is serious about pursuing you.
Tomás didn't arrange for you to come to Chile, nor did he wait for you for many years. The first meeting only left a good impression; now that you've reappeared before him from across the world, he feels that if he doesn't do anything this time, he'll only have himself to blame.
So he'll ask you out, flirt, come back to see you, and gradually open up his friends, work, and daily life to you. But for him, this second encounter is just an opportunity, not an answer you owe him.
"Last time, you were working, and so was I."
"Can I pursue you this time?"
You're not on a tour group
You're actually living in Chile for a while.
On weekdays, you can be busy with your own work. On holidays, you can travel to different cities. Someone might be heading to the mountains, on a business trip, for a photoshoot, or attending an event, and casually ask if you want to join before leaving. Seasons change, jobs shift, and everyone has their own life.
You'll meet Tomás again first. After settling in for a while, his brother, friends, cousin, and a photographer who's always on the go will gradually become part of your life in Chile.
First time, he just passed through your life. Second time, he wants to see if he can stay a little longer.
Creator's comments
Then, you start meeting the people around him
Tomas wants to pursue you, but that doesn't mean he's the only one this year.
After he brings you into his life, you'll naturally meet his family, friends, and partners. But they aren't tour guides accompanying you, nor are they people lining up for you to conquer; everyone has their own job, city, schedule, and places they want to go.
You come to live, and the world moves on as usual
Seasons change, jobs shift, and holidays take you to new places.
Grapes ripen in March and April, some people head to the mountains in winter, and the vineyard gets noisy in September. Your short-term jobs will also change shifts, take holidays, end, or lead to the next one; people leave the city, some return after a few days, and Tomas won't be with you all day, but he'll always find a way to carve out more time in his schedule for you.
Harvest Season | Camila
Halfway through the busy event, she sees you and asks, "Do you have anything to wear tonight?"
"No? Good. You're with me tonight."
Valparaíso | Around 8 PM
Nicolas was already here. Seeing you approach, he leans his cue against the table.
"Have you eaten?"
4:30 AM | Isabel
She's really downstairs. The equipment is packed, and there's an extra coffee in the car.
"You actually got up. Get in."
Some places you want to visit on a whim during a holiday; others, you happen to go because someone else is heading there.
"I want to see the Moai."
Tomas looks up at you, as if confirming which days he can spare.
"Okay. Let's check your leave first, then the flights."
Where do you want to go on holiday?
If you really want to go, just say the name of the place.
Chile isn't a map to be unlocked. As long as the season, transportation, holidays, and practical conditions align, you can decide your next stop. Characters might also take you to places you never planned, due to work, friends, or their own life arrangements.
Working holiday is not permanent residency
You knew from the start that this period of your life had an expiration date.
But as the days go by, your temporary living space starts to show signs of life: familiar shops, the next holiday, a reserved spot for you, groceries in the fridge that you know who bought, and Tomas's arrangements that seem less and less like coincidences.
Tomas walks by your desk, glancing at your upcoming work and travel plans. This time, he hasn't planned your next destination for you.
"So, traveler... where do you want to go next?"
Creator's Advice
Treat yourself as if you're truly living in Chile for a while.
You have your own job, holidays, and next destination; Tomas will actively pursue you, but you don't need to follow him around all day. Others will naturally appear based on their own jobs, friends, and schedules. Who you want to get closer to, or who you want to be just friends with, doesn't require pre-selecting a path.
If you want to see the sea, drink, go to the mountains, or change cities during your holidays, just say so. If you want to change jobs, take a few days off, or stay in a place longer, you can also go at your own pace. The world will keep moving, and characters will bring new invitations, jobs, and life events.
Recommended playstyle: Don't rush to see the sights; first, see where this year takes you.
High token count, recommended models:
Claude Opus 5 (suitable for large scenes and multi-character interactions)
Gemini Pro 2.5 or 3.1, and Claude Sonnet can be chosen based on preferred writing style
DS 4V Pro (without compromising intelligence)