• One More Sidequest Dating Deck with real-life challenge cards for playful dates and deeper connection
  • One More Sidequest Dating Deck with real-life challenge cards for couples
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Dating Edition

Dating Edition

A deck of 50 playful sidequests designed to reveal chemistry without awkward small talk

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€25,00 EUR
€25,00 EUR
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You’ll learn more from one slightly ridiculous adventure than from ten perfectly planned dates.

This deck throws out scripts, small talk, and “so what do you do?”
Instead, you do things together that and see what actually happens.

Do a sidequest together whenever a date night starts to feel scripted.

Best used for:

  • First dates, second dates, third dates… you get it
  • Long-term couples stuck in routine date nights
  • Creating intimacy through shared experiences
  • Seeing how someone moves through the world, not just how they talk about it

Also works surprisingly well as a gift, especially when you want to say “let’s do something different” without saying it out loud.

After this drop, we’re not printing the Dating Deck again for a while

What kind of sidequests are in this deck?

The Dating Deck is built around shared experiences that naturally lead to meaningful conversation.

Each card combines:

  • A real-world sidequest you complete together
  • A reflection prompt that helps you talk about the experience you just shared

The sidequests range from:

  • Playful and silly (games, challenges, role-play)
  • Creative and curious (making, building, imagining)
  • Gently uncomfortable in a safe way (trying something new, being seen)
  • Quietly intimate (presence, attention, shared reflection)

The prompts aren’t random questions, they’re directly connected to what you just did, making conversations feel natural instead of forced.

In short:

You do something first. Then you talk about what it revealed.

Is this the right deck for me?

This deck is for you if:

  • You want deeper connection without turning dates into interviews
  • You believe shared experiences say more than small talk
  • You’re open to reflecting together, but don’t want therapy vibes
  • You enjoy a mix of playfulness, honesty, and emotional curiosity

It might not be for you if:

  • You want purely surface-level activities with no reflection
  • You’re uncomfortable with open conversation at any level
  • You’re looking for structured relationship advice or problem-solving

The Dating Deck isn’t about fixing anything, it’s about understanding each other through experience.

How you’ll actually use this deck

This deck fits into time you already spend together.

How it works:

  • Shuffle the deck together
  • Draw one sidequest
  • Do the activity at your own pace
  • Use the prompt on the card to talk about how it felt

The prompts are:

  • Optional — skip or adapt them anytime
  • Designed to feel safe, open, and human
  • Focused on reflection, not interrogation

You’ll use this deck:

  • On date nights
  • During weekends or trips
  • At home or out in the world
  • Early in dating or years into a relationship

Each card gives you something to do together and something meaningful to talk about after.

What's in the box?

  • 50 Dating Sidequest cards, each with:
    -One shared challenge
    -One reflection prompt tied to the experience
  • 3 info cards (introduction + how to play)
  • Premium card stock, designed for repeated use
  • Rigid magnetic box, built to last

This deck is standalone, no other Sidequest deck needed.

View full details

All Our Sidequests

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Frequently Asked Questions

Before you start your next Sidequest

What exactly is One More Sidequest?

It’s the nudge you didn’t know you needed.

One More Sidequest is a lifestyle brand creating decks of real-life challenges designed to help you feel something again. Whether that’s connection, discomfort, creativity, or just the thrill of doing something you wouldn’t normally do on a Tuesday.

Who is this for?

It’s for anyone who’s stuck in a loop and craving a plot twist.

For the creatively burned out. The recovering overthinkers. The emotionally brave weirdos. The secretly adventurous. The people who want more aliveness in their lives, but don’t know where to start.

If you're tired of doomscrolling, tired of doing nothing, or tired of doing too much that means nothing… this was made for you.

Is this a game or a self-help product?

Neither. And a bit of both.

It’s not about fixing yourself, optimizing your life, or becoming “better.”

It’s about doing - experimenting, playing, and breaking routine in real life.

Think of it as structured spontaneity.

Do I need to play with friends?

Nope. You can solo quest or recruit party members (a.k.a. your crush, roommate, barista, or dog).

Some cards are introspective, some are social, and some are slightly unhinged. It’s very much a "choose-your-own-vibe" type situation

How long does one Sidequest take?

Anywhere from a few minutes to a full day of adventure.

Some quests fit into a lunch break. Others turn into a whole afternoon.

You decide how deep you go. The card is just the spark.

Is this a one-time thing or replayable?

Very replayable.

Every deck contains dozens of different Sidequests, and no two people complete them the same way. You can draw randomly, pick intentionally, repeat favorites, or remix them with friends.

What’s the difference between a regular deck and a mini-deck?

The regular deck is the core Sidequest experience.

Mini-decks are experiments.

They explore new types of challenges, sharper themes, and bolder ideas that don’t belong in the main deck. This is where we test new directions and see how far Sidequesting can stretch.

Can’t I just make up my own challenges?

Totally. But let’s be honest, if you were gonna do that, you’d probably have done it already.

One More Sidequest exists to get you moving without overthinking. It takes the planning out of doing something cool or weird today.

Every card is a tiny step toward living a bigger story and the best part is you’re not doing it alone. There’s a whole community here chasing their own sidequests too

When will my order ship?

Orders from this drop will be shipped from Sidequest HQ 1-3 business days after you place an order.

It’s just the two of us running this thing (Reio and Aisha, hii) packing decks by hand, double-checking orders, and trying not to mess up shipping labels at 2am.

Tracking hits your inbox the moment your Sidequest leaves our HQ.

Do you ship internationally?

Right now, we ship Sidequest decks to EU countries only.
Including UK, Iceland, Norway and Switzerland.

We’re keeping it simple for now so we can actually deliver a good experience (and not lose packages to customs limbo).

Expanding the decks beyond the EU is something we want to do, but if you still want to sidequest from anywhere in the world, we have something for you. Check out the Sidequest Mail Club

What's the difference between the decks and Mail Club?

The decks are about adventure.

Mail Club is about transformation.

The decks give you 50 sidequests to help you break out of routine, try new things, and create stories worth telling.

Mail Club takes a more focused approach.

Each month explores a single theme through a personal letter, reflection prompts, and an exclusive sidequest designed to help you experience that idea in the real world.

The decks give you dozens of different adventures. Mail Club invites you to go deeper into one each month.

Is there a card that makes me text my ex?

No