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Our Story 5 min read September 18, 2026

I Wrote 1,518 Questions for My Girlfriend

Every prompt in Together's daily challenge came out of a text file on my laptop. Here's what I learned writing them - and the ones that didn't make it.

By Dominik, founder of Together

Together has a thing called the daily challenge. One shared prompt a day, and neither of you sees the other's answer until you've both replied. That last part is the whole point - it's not a question you answer at someone, it's one you both have to show up for.

Which means the app needs questions. A lot of them. Right now there are 1,518 of them, and I wrote every single one. I thought it would be the easy part. It was not the easy part.

Rule one: it has to work when you can't touch each other

The first hundred questions I wrote were quietly useless. "Cook dinner together." "Go for a walk and talk about your week." "Hold hands and..." - you get it. Every one of them assumed two people in the same room.

My girlfriend and I are in different countries. I was writing prompts that our own app couldn't give us.

So that became the first rule, and it's the one that cut the most: every prompt has to work for people who are thousands of miles apart. Not "adapt okay." Work. If a question only makes sense on a sofa, it's out.

What survives that rule is more interesting than what doesn't. "Show me whatever is making noise around you right now" works at any distance. So does "Show me the last thing you wrote by hand." You're not simulating being together - you're doing something you genuinely can only do apart, which is see a slice of a day you're not in.

Rule two: no assumptions about the relationship

The second thing I stripped out was everything that assumed a particular kind of couple. No marriage, no kids, no living together. Not because those couples don't use the app - plenty do - but because a question that assumes a life you don't have doesn't just miss, it stings a little. "What's your favourite thing about our apartment" is a bad question for most of the people I built this for.

Rule three: it has to survive being translated thirteen times

This one I didn't see coming at all.

Every prompt exists in thirteen languages, actually written out rather than machine-translated at runtime - a couple in Japan getting a silently English question is worse than not having the feature.

Which quietly bans a whole category of writing. No puns, no idioms, no wordplay, no brand names. Anything that leans on an English turn of phrase is either nothing or nonsense somewhere else, and I lost a few I liked that way. The prompts that translate cleanly tend to be the plain ones. Turns out plain was better anyway.

The voice took longest to find

Early drafts were written like a form. "Describe your ideal weekend." Nobody wants to fill in a form with someone they love.

What worked was writing every prompt as if your partner is the one asking. Not "describe a time you felt appreciated" but "what makes you feel most loved by me?" Same information. Completely different thing to receive on a Tuesday morning.

Once I switched to that voice, I rewrote most of what I already had. Some I like best now:

That last one isn't a question at all - it's a dare, and it's the one I was most nervous about shipping.

Not all of them are questions

Partway through I realised a text box was the wrong shape for a lot of what I wanted to ask. So the challenge grew other types: this-or-that with a guess at what your partner picked, a drawing, a photo, a slider, a dare you both mark as done. "Draw us on a road trip" is a worse question and a much better prompt.

What writing 1,518 of anything teaches you

Mostly that the good ones are specific and the bad ones are grand.

"What do you love about us" is a question nobody can answer before coffee. "Show me something you wear almost every single day" gets you a photo of a hoodie and a story about where it came from. The small one wins every time.

I also stopped trying to write questions that would produce a beautiful answer. The ones that land are easy to answer honestly in about fifteen seconds. Depth isn't something you can request - it shows up on its own, on the days it wants to, usually attached to something mundane.

There are more coming. I still keep the text file open.