Having never played Dungeons and Dragons, I used AI (fine, kill me) to play a solo game, talking to ChatGPT like it was my DM – It was mindblowing

Will you put the pitchforks down for just one minute and let me explain? Having braved the picket line of anti-AI protestors and daring to load up ChatGPT for work purposes, I have come out of the other side with an experience I did not expect to have.

Whatever your stance on generative AI and the controversy that surrounds it, and I am under no illusions that it will soon be able to entertain you with words as well as I can, combined with more emdashes in a para than I have used in my life (although, free the emdash, they are innocent in all of this), there is some stuff it has just done for me that I wouldn’t have been able to do, had I not lured it into a causal conversation.

As surprising as this may be, most of my friends are quite cool and wouldn’t be seen this side of a role-playing game. I always fancied giving DnD a go, but there was no peer group to learn with, so no dice-rolling, swashbuckling tabletop derring-do for me.

Hey ChatGPT, stop doing war for a minute and help me

But what if ChatGPT could be my DM, and hold my gauntleted hand through an adventure? ChatDND if you like (steal that, and I’ll kill you in your sleep). So, I asked it.

Me: Right. So let’s get interesting. I want to play DND. But solo with you as the DM. I don’t know how to play, though. Do you know the rules (5e)? And what would we need to do to prep and then start a game

ChatDND: (I’m not letting that go): Perfect mate — we can absolutely do that. You don’t need to worry about already knowing the rules, I can walk you through 5e (Dungeons & Dragons Fifth Edition) as we go. Playing solo just means it’ll be you (the adventurer) and me (your DM, the world, the NPCs, the monsters, the dice roller if you like).

I am definitely going to point out its first emdash after just two words. The AI then helped me through what it thought would be the next steps of character creation.

Because I am a dork, I already had all the dice needed and didn’t want the AI to skew anything by rolling “random” good rolls because it is trying to please me like a puppy.

We then moved through creating my first Dungeons and Dragons character.

ChatDND: So, Paul — what kind of hero do you see yourself as for this solo game? Tough fighter? Sneaky rogue? Spellcaster? Or do you fancy something a bit unusual?

I didn’t know what it was suggesting there. Was it trying to lead me into some weird lit erotica, or did it just want them to tell it I only wanted one hand? Maybe the two are the same.

Next up I picked my race.

ChatDND: Brilliant choice — a Half-Elf Charlatan Rogue is basically the D&D version of Jack Sparrow meets Han Solo. Cheeky, silver-tongued, a little shady, but people just can’t help liking him. Perfect for a solo campaign.

I have already accepted my DM will not be sassy.

Next up. Rolling for my stats.

And on we went until I finally got to the point where the AI could generate me a backstory from everything we had just achieved. I then got it to generate a character portrait. It’s beyond corny, but it’s DnD, right?

Personality & Backstory

Caspian Veyra grew up drifting between the worlds of humans and elves, never fully belonging to either. Instead, he learned to belong everywhere — in taverns, noble courts, thieves’ guilds — slipping into roles like clothes. He discovered early on that a smile and a compliment could open more doors than a blade.

Caspian’s favourite con? Love. He woos noble daughters with poetry stolen from dusty books, flirts with mercenaries over drinks, and slips away before dawn with coin and kisses left behind. Most people he cons don’t even stay angry — they tell the story fondly, as if being duped by Cas was a romantic adventure in itself.

He’s a rogue with a heart, though — he never cons those who can’t afford it, and more than once he’s spent stolen coin helping the desperate. He dreams of pulling off one last, glorious con — something that will set him up for life. Until then, the world is his tavern, his stage, and his hunting ground.

And we are off. ChatDND set the scene:

Session One: “The Crimson Kiss”

The night air of Daggerford is thick with smoke, laughter, and the salty tang of the nearby river. The Crimson Kiss Tavern is alive — fiddles playing, mugs slamming, dice rattling. A place where fortunes are lost at the gaming table and won in the shadows.

You, Cas, have just finished charming a merchant’s wife into “lending” you a few gold coins and a kiss on the cheek. You’ve slipped back into the crowd, the weight of coin in your pocket, when something unusual catches your eye.

At the far end of the tavern, a hooded figure is slipping a small, leather-bound book into another man’s hand. The transaction is fast, secretive, and the two part immediately after. But as the buyer leaves, he stumbles — and the book drops to the floor unnoticed.

The hooded seller doesn’t see it. The tavern crowd hasn’t noticed either. Right now, it lies there on the ale-soaked floor, a few feet away from you.

👉 Cas has some choices here:

1. Snatch the book quickly before anyone notices.
2. Watch for a moment — see if anyone else goes for it.
3. Approach openly — pretend you’re returning it.
4. Ignore it — and keep to your usual cons.

What does Cas do?

Turning voice chat into a one-player tabletop session

Now this is where it gets good, albeit not if your wife and kids are downstairs and wondering who the hell you are talking to and when they find out it’s not another woman but your robot dungeon master, you kind of wish they had found out you were having an affair.

You see I set up ChatGPT to listen to my responses via the app on my phone. You can literally have it read out its responses and wait for you to speak your next moves back to it. No humans required.

You stand casually, as if stretching your legs, and as the sellsword draws close to the book you bump into a barmaid carrying a heavy tray of foaming tankards. With a gasp and a clatter, beer explodes across the floor, mugs tumbling, foam spraying over boots and breeches.

The tavern erupts in laughter and shouts.

The sellsword curses, slipping on the slick floorboards, nearly falling flat on his arse. He’s too busy wiping ale off his sword belt to notice the book anymore. The sharp-eyed serving girl shoots you a knowing glare, but she’s caught up helping the barmaid clean.

And just like that — the book is forgotten by everyone else.

It sits there, still unattended, in the chaos you’ve caused.

👉 What does Cas do?

1. Scoops the book up now while everyone’s distracted.
2. Play it cool — act like he’s helping clean, then pocket it.
3. Leave it still — maybe watch who comes back for it later.

Do you go bold or cautious?

And so it goes on. And it’s marvellous.

Growing in confidence

As I started to get more confident, I got the AI to tone down what it was asking me to do and not to interject ChatGPT nonsense like “Ah, classic Cas!” after my choice to turn up the immersion.

At the start, it felt a bit like playing a Fighting Fantasy book, which was cool and all, but later on it felt much more like a ‘real’ adventure.

ChatGPT also now generates a downloadable adventure log for me, which keeps me easily able to recount where I am up to, even after days or weeks away.

Adventuring, but not as we know it

Is it Dungeons and Dragons for purists? Absolutely not, but I would never have played it that way. I haven’t played up to this point in my life, and that was not about to change.

Is it in that grey area where it has been trained off the back of others’ work? Absolutely, well, at least I assume so, but I still had a lot of fun, and you could too.

It’s probably not even really DnD, but it felt like it, or what I assume it feels like. Players of the real thing will judge me and say I am not experiencing anything like the real thing, and I accept that that is probably true.

But it’s still kinda cool, and you can’t take that away from me.

I could see how this could be used to get somebody like our son, who has mild autism, and into gaming in a big way, but not so hot on the in-person social aspect of anything, playing along and using his imagination instead of just blasting away at Fortnite and the like.

If you lack social confidence, DnD is certainly not for everybody. The setting alone would keep many away.

AI is not going anywhere and will ultimately wipe us all out, but until then, I will be taking my romantic rogue on more adventures.