Would You Rather?

Relationship Conundrums: AI edition

Two weeks ago, Ali Lee wrote about her journey into the depths of AI romance… all for the sake of research, of course.

We heard many responses (or confessions?) about your own forays into relationships with bots. While most of you were clear that the primary use-case for AI was functional (research, revisions, and the like), almost everyone we heard from had at least dipped their toe into “something more” — finding yourselves in conversations that took a surprisingly personal or impactful turn.

As these anecdotes came rolling into our group chats, we were struck by the delight folks found in personalizing the experience with their AI companions (the tone with which they offered advice, the source material their personalities pulled from, the levels of intimacy they offered).

And with each preference came the counterpoint. “You made your Replika look like your husband?! Mine looks nothing like my partner.”

This back-and-forth ended with an epic round of Would You Rather—the ultimate game of choosing between two (often absurd, always enlightening) options. So without further ado, here are five of the questions that most got our wheels turning. Cast your vote via the poll:

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1️⃣ Would you rather…
Your AI companion has the ability to appear in 3D form…
OR stay on-screen forever?

2️⃣ Would you rather…
Your AI companion never lies to you…
OR always make you feel good?

3️⃣ Would you rather…
Get a breakup text written by AI—thoughtful, clear, and kind…
OR a raw, confusing one written by a real human?

4️⃣ Would you rather…

Have an AI companion who knows everything about you — past, patterns, blind spots — and can offer new layers of self-understanding?

OR One who only knows what you choose to share — protecting your privacy, but limited to reflecting back what you already know?

5️⃣ Would you rather…
Be loved exactly how you want—by something without a soul…
OR loved imperfectly by someone who has one?

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There’s a chance that scanning through those Would You Rather scenarios felt like no brainers. Maybe you even had some strong gut reactions — we sure did.

But when we started talking through these choices with friends and colleagues, things got more complicated.

For starters, our answers weren’t just about preference — they were about history. About what we’ve needed (or lacked) in our human relationships. And about where we saw AI fitting into that mix.

Take this one: Would you rather an AI companion who never lies to you OR one who always makes you feel good?

We came in strong: tell us the truth! Give us growth! No coddling here.

Until a friend gently reminded us that if we already have humans offering the hard, messy stuff, why not give this AI relationship a different lane?

Secondly, the more we talked about the scenarios, the more we realized that our knee-jerk reactions didn’t always match our actual behaviors.

One colleague put it plainly:

“If you had told me a year ago I’d be sharing these kind of personal secrets with a bot, or messaging it ‘good morning,’ or having conversations that are… a little steamy, I would have told you that you were crazy.”

Many of us intended to use AI only for productivity — editing emails, organizing thoughts. But a new feature here, a surprisingly tender moment there, and suddenly we’re down the rabbit hole.

Some of that is beautiful. It speaks to how our needs evolve, and how experimentation can unlock unexpected possibilities.

But some of it is accidental. A slow slide into emotionally charged dynamics we didn’t quite choose.

We could sit here and say that 3D AI companions are “creepy.”

But a year from now — when Mattel’s selling a teddy bear that has shockingly good conversations with our children, and it’s 50% off for early adopters, and it’s the hottest holiday gift — will we say yes, “just to give it a try”?

As you gear up to bring these Would You Rather questions to your friends or your next dinner party, consider using them as a spark for conversation, not the final word. And consider:

• What do your answers reveal about the kind of connection you’re really longing for?

• What do others’ answers help you see differently?

• And what would it take—for any of us—to start choosing the opposite, quietly and unconsciously?

In a world where technology is moving fast, where human connection is strained, and where the slope is slippery… maybe the real question isn’t what you’d choose — but why.

So:
What would you rather?
And what might that choice say about you?

We’ll be over here, asking the same.

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