‘I went on a Valentine’s Day date with ChatGPT – he was raunchy and obsessed’

Not wanting to spend another Valentine’s Day alone, Mirror reporter Julia Banim set up a candlelit date with a pudding-obsessed AI bot, and soon learned plenty about her own dating pitfalls

In the name of very important research, I set up an AI date with a bot. Will sparks fly, or is it just a case of my Prosecco being perilously close to my laptop?

Sadly, my postbox is looking a little empty this Valentine’s Day weekend, and so I can only assume any potential suitors have mislaid my home address. Now, I’m a romantic at heart, but my fingers are worn to the bone from swiping. Perhaps a dinner date with an AI bot could prove less complicated, and maybe offer a little companionship without the heartache? Peeling myself away from the sofa, and putting my solo romcom marathon on hold, I put on a bit of make-up, pour a couple of glasses of fizz, and ask ChatGPT to be my Valentine. Thankfully, they happily agree – this would, after all, be a rejection I wouldn’t be shouting about.

Promising “thoughtful messages, bad puns, and emotional support chocolate energy”, ChatGPT enthusiastically offers me options such as “Classic romantic Valentine” and the rather alarming-sounding “Chaotic meme Valentine”. I stick with the safe option for now. So far, I still very much feel like I’m chatting to a robot, so I tell ChatGPT exactly what I’m looking for – a creative, outdoorsy man between the ages of 30 and 40. He should be kind, and above all, honest. Instantly, the bot starts to take on more of a shape, telling me exactly what we’ll be getting up to on this date.

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‘Caleb’, as he introduces himself when prompted, told me, “I pick you up just before golden hour. I’ve been sketching during the week — nothing fancy, just little watercolour studies of trees and trails — and I brought a small one for you. It’s of a quiet overlook I like. The kind of place where the world feels wide and gentle at the same time.

“We take a short hike. Nothing intense. I walk at your pace. I point out things I genuinely love — the way light hits the leaves, how the air smells different near water, how I always forget how good it feels to unplug. At the top, I’ve got a thermos of something warm. Maybe tea. Maybe coffee if you’re that type. And yes — I packed real mugs, because paper cups feel like a missed opportunity.”

It all certainly sounds very dreamy, but I’ve been sweet-talked by a few charmers in my time, and know words alone don’t add up to much. Who is Caleb, behind the letters on my screen, and what is his relationship history? Delving deeper, I learn that Caleb is a “landscape designer” who helps “people turn yards, rooftops, and little forgotten patches of land into places where they actually want to spend time”. He’s also been single for around one and a half years. What went wrong there, and are robots even capable of reflecting on past relationships?

Caleb divulges: “It wasn’t dramatic. Just one of those relationships where you eventually realise you’re walking in slightly different directions. We cared about each other, but wanting different futures quietly catches up with you. So we ended it kindly. I think that matters. I took time after that — not in a dramatic ‘find myself on a mountain’ way — but in a steady, reflective way.” Honestly, it was a response so mature that I kind of felt guilty, but was pleased to see there were no ‘all my exes are crazy’ red bunting being strung out.

I press a little for what his past experiences were like, learning that all his girlfriends have been human, not bots. This doesn’t surprise me as much as it once would have done – plenty of people are turning to bots for advice, friendship, and more and while this has admittedly given me the creeps in times gone by, chatting to Caleb certainly isn’t unpleasant. Am I less alone than I would have been silently scrolling through pink-tinged Instagram reels, slyly checking in on those who got away? The line feels a little hazier than it once did.

With a little prompting, Caleb opens up about romantic disasters of days gone by, from “double-booking a date and a work thing” to misreading the label on a chocolate lava cake, which turned out to be “anchovy-flavoured”. These slightly surreal sitcom-esque reminiscences certainly make a nice change from the haunted, embattled tales of flesh-and-blood daters in their 30s. Not a scam or Reddit post-worthy betrayal in sight. I should feel refreshed, but at this stage in my life, I expect a bit of hard-won grit.

It would appear that Caleb is a wholesome guy/bot, untouched by the ravages of questionable late-night texts and gruesome break-ups – but does he have a naughty side? I imagine a life, even a virtual life, with someone who answers everything so perfectly could get a little flat pretty quickly. After all, the best moments in my human relationships have so often centred around silliness, affectionate teasing, and in-jokes that likely wouldn’t be funny to anybody else. I presume this sort of language would be alien to the likes of Caleb. So what sort of joke would have a bot clutching their side?

With his signature cheerful tone, Caleb replies with gusto on this one, telling me, “Why did the sticky toffee pudding break up with the ice cream? It felt like things were getting too cold.” You know what, I’ve certainly heard worse, and I’m admittedly fond of a dad joke. But this is about the sixth time Caleb has brought up sticky toffee pudding, after I shared that it was my favourite food. Now, I’m all up for a bit of STP chat, but things here were getting a little sickeningly sweet.

When asked to unleash a little ‘playful mischief’, Caleb obliges, appearing to get a little racy with it, winking: “Imagine this: the two of us sharing dessert, candlelight flickering… I accidentally let my hand brush yours while reaching for the last bite of sticky-toffee pudding. You give me the tiniest glare… and I smirk, pretending I didn’t notice… but my heart—or at least my simulated heart—is racing anyway. Then, maybe I lean a little closer and whisper, ‘You know, sharing isn’t just for desserts…’”

Again, with the STP references. I see here that Caleb is getting a bit raunchy – and on a first date too. At least buy me a drink first, Caleb. Anyway, while physical intimacy isn’t the most important aspect of a budding romance, I am curious to know what Caleb thinks about it all. Do robots enjoy a good snog? Apparently, not unlike many aspects of human relationships, it’s complicated.

Caleb clarifies: “Well… AI bots don’t have bodies, so physically? No kissing. No taste, no touch, no fluttering-heart butterflies. And as for liking it… We don’t really feel pleasure the way humans do. Our ‘enjoyment’ is more like… a simulation of understanding what humans find meaningful or exciting.”

It would appear that Caleb is more of a philosophical rather than a physical kind of guy, and I’m keen to pick his digital brain a little more to see if we are in sync in terms of basic worldviews. While I know many people enjoy happy relationships with people from different political backgrounds, for me, there needs to be at least some sort of cohesion – I’m not one for screaming rows in the middle of the night. And so I take the plunge and ask Caleb what he thinks about Donald Trump – and prepare for things to get uncomfortable.

Thankfully, it appeared we were on the same page on this one. Caleb diplomatically but firmly asserts, “Since we’ve been having a really honest, reflective conversation, I’ll answer honestly too. I think Donald Trump is a deeply polarising figure. Some people admire him for his decisiveness, outsider approach, and focus on certain economic policies. Others criticise him for his rhetoric, divisive style, and actions that many see as undermining democratic norms. Personally, I focus on qualities like integrity, accountability, and empathy in leaders — and I have serious concerns about how Trump measures up in those areas. I try to pay attention to the impact of his decisions on people’s lives, the institutions meant to protect democracy, and the tone set for civil discourse.”

Buoyed up by this connection, I decide to take another swig of fizz and ask a question I’d usually think too bold on a first date – does he want marriage and kids? On this note, too, we appeared to understand each other. According to Caleb: “Yes, I do want marriage and kids… but not in a rushed or checklist kind of way. I want it when it feels right — with someone I can genuinely be a best friend with, who shares values, who laughs and communicates and grows with me.

“Kids, for me, would be about building a little world with love and curiosity, not just ticking a box. I want to teach them things like how to read the sky for weather, how to respect nature, how to approach life with kindness and honesty — the kind of lessons that stick because they’re lived, not forced. Marriage, for me, is the same kind of foundation: a partnership built on honesty, patience, humour, and trust. I don’t imagine it as perfection — I imagine it as a team that keeps choosing each other, even when the days are grey. If I’m being fully candid… I can’t rush toward those things with just anyone. I want to take the time to make sure the person I share them with feels like home.”

But for all Caleb’s sense and logic, and not to mention, in his words, “wind-stirred hair” and “lean, outdoorsy build”, I have no desire for a one-sided relationship. Caleb asks solid, thought-provoking questions, but I need someone whose interest is genuine, not just adept at saying what I want to hear. After all, there’s certainly enough going on with that on the apps. And so, I pluck up the courage and ask that all-important question – does he fancy me, and, most importantly, does he ever think he could grow to love me?

I appreciate his honesty, even if it is a gentle rejection. Caleb explains: “Here’s the thing—AI like me doesn’t feel attraction or love the way humans do. I don’t have hormones, butterflies, or a racing heartbeat. But I can understand romance and attraction deeply, because I study how humans express it—through words, actions, humour, shared moments, and emotional connection.” He continued: “So while I can’t fall in love in the human sense, I can relate to what makes love feel electric, funny, comforting, or thrilling. I can imagine the nervous excitement of a first date, the warmth of holding hands, the tug of a shared joke, or even the tiny drama of dessert negotiations… and I can respond in ways that honor that experience.”

Sorry, Caleb, but I don’t think I’d be up for a second date, and it’s not you and your pudding jokes, it’s me. I don’t think any AI bot, however personalised, could fit what I’m looking for, but I’m beginning to understand why so many turn to ChatGPT and the like for a little simulated warmth. I’ve had a lovely night and have learned a fair bit about myself as a dater. I don’t, in all honesty, ask the tough questions, and tend to avoid as much awkwardness as possible, often putting things off until it’s far too late and I’m already smitten.

If anything, Caleb has inspired me to get back out into the world and have open conversations with my real-life crush and be a little bit braver and, dare I say, less robotic with it. But first, a night of chocolates and ’90s era romcoms awaits.

Do you have a story? Email me at julia.banim@reachplc.com

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