Allegra and Charlie

As Dorothy said to her little dog Toto, we’re not in Kansas anymore. We are, in fact, in Bristol. Yes, we have finally managed to break free of London’s stranglehold, escaped the M25 and now the west is going to show us how they do it. How do I know we’re in Bristol? Well, it’s like those TV shows that want to remind you they’re taking place somewhere fabulous and amazing but don’t actually want to pay for any on-location shooting, so intercut scenes with sweeping stock footage of the Eiffel Tower, or Tower Bridge, or the Chrysler building. Anyway, in lieu of grainy film of the Clifton suspension bridge, or a bus that says ‘Portishead’ on the front, today’s daters remind us we’re in Bristol by… saying so every few lines. Contractual obligation, perhaps.

Our Bristolians are Allegra, 20, a dental student – this will become very important as the hours drag by reading this – and 24-year-old Charlie, a trainee solicitor. Spoiler: you absolutely will pinch and zoom on your phone to look more closely at Charlie’s teeth later, trust me. Here they both are in their finest floordrobe:

Before we get stuck in, and see if you can guess how this one is going to go.

Allegra on Charlie | Charlie on Allegra

What were you hoping for?
A fun time, good food and an interesting story.

Maybe they should stop asking them this. Does anyone answer it with even an ounce of originality? Ooh you were hoping for “good food” when you went to a restaurant? Why have I never thought of that? Every so often I fall out of love with one of the questions and let’s just say this one and I are now in separate bedrooms and I’ve alphabetised all the novels I’ll be claiming in the divorce.

Actually, hang on.

What were you hoping for?
Specifically, not a 20-year-old student.

Miaow. Charlie’s audition for the next series of RuPaul’s Drag Race starts here. Surely we need an Alexis gif here – she would be very pleased with that one.

First impressions?
Friendly, nice eyes, a little nervous.

Did you go back to have a look at the eyes? Same. Not bad, I guess. I don’t go very gooey over people’s eyes. The loveliest eyes I’ve ever seen belonged to my childhood dog (now deceased).

First impressions?
Great dungarees.

Does he mean “great dungarees!” or does he mean he’s pulling a Chandler Bing face (Friends reference! I am very millennial!) and saying “great dungarees”.

What did you talk about?
The Bristol food scene, cooking, dentistry, his lawyering, how we are both sarcastic and the awkward situations it gets us into. There were a fair few pictures of his very cute niece, and many pictures of my brother’s wedding.

Dentistry, Bristol v London, the perennial dogs conversation, more dentistry, her food Instagram, her Instagram detailing the horrid things boys send on Tinder, and a bit more dentistry.

Dentistry ✅ ?
Bristol ✅ I love that they do this, especially the Bristol vs London thing – I’m assuming they are actually both Londoners – because it’s like overhearing two of your exes talk about how they don’t care about you and never think about you all… for five whole hours.
How we are both sarcastic blah blah – do you know how many times I heard, as a younger man, the old adage that “sarcasm is the lowest form of wit”? Oh it was a lot, a hell of a lot. I don’t think, from the age of 13 to, oooh, 39, I gave a straight answer to anything. Every statement posed, every question asked, was a spotlight upon me, my chance to bring the house down. I can now say with some authority that I must have been even more exhausting to be around than I am now, because, while sarcasm is actually very amusing, if it is your default setting, if you are always ‘on’, it becomes tiresome very quickly and people will, eventually, stop asking you anything. Like, the Olympics, or series of Line of Duty, or sex with your brother’s husband, it’s better to have a decent break in between – you appreciate it more.

Why does she have so many Instagram content strands? I mean, miss me altogether with the food one. As for the Tinder one, I do think it’s important to call out bad behaviour on dating sites, but I don’t think it changes anything. I don’t think the men – it’s always men – take the advice to heart other than to complain ‘we’re not all like that’ because they don’t see that behaviour in themselves. I’m not talking about Allegra’s account here because I haven’t seen it – no doubt a mysterious anonymous benefactor will drop me a link before Strictly starts – but I think while those kinds of exposés are important, the ones screenshotting people who aren’t attractive or particularly articulate, often invading a supposedly safe space, aren’t that great.

The irony of my saying this after over five years of gently eviscerating countless young hopefuls on these very pages of the internet is not lost on me. Please don’t write in.

Any awkward moments?
Maybe when he said he hadn’t been to the dentist in three years.

I felt quite self-conscious about my metallic filling.

I have questions. Did she ask him when he last went to the dentist? Or did he volunteer this information? Either way, stop this! You do not have to relate every aspect of your conversation to your or your date’s job!

Do people out with paramedics do this?! “Wow, I haven’t been involved in an RTA – I believe that’s the correct term – for about a decade now.” Do opticians interrogate dates about their eye health? Supermarket checkout operators, perhaps, love to be quizzed on the most difficult thing to scan (a Cadbury’s Creme Egg, probably). I know we are hardwired to talk about our profession as if it were one of our vital statistics – “Hi, I’m Sue, I’m 49, and I manage a juice bar in Alderley Edge” – but it’s not all there is.

Good table manners?
Pretty good, although a bit weak, because he didn’t finish his pie.

Excellent. And she was quite sympathetic to me struggling to navigate the sourdough starter.

The table manners question seems to be enjoying a resurgence, after years of “Impeccable” or dreary politesse about chopstick usage, starters-sharing, and being good at topping up the wine glass – which all sound like stage directions from an episode of Doctor Foster. Instead, we’re getting to see people’s frankly bizarre stances on table etiquette. Two dates recently have commented that it is rude to actually get up to go to the toilet before you have finished eating – imagine what their childhoods must’ve been like – and now Allegra says Charlie’s table manners were “weak” because he didn’t finish his pie.

First of all, can table manners be “weak”, like a handshake, a joke, or a smile? I’m unconvinced, unless it’s Bristolian street-slang that Allegra has heard someone say, as she swept past them while they stood smoking in the All Bar One doorway. And as for not finishing your food: you have left home now, Allegra, it’s okay not to eat everything. I know you were probably made to sit at the table until four in the morning when you finally ate that last forkful of foie gras, but now you’re an adult you can be as wild as you want and say, when you have had enough, that you can’t finish it. Eat the pie, leave the pie, nobody cares.

I don’t know what the hell Charlie is on about with his sourdough starter. Navigate? Was it a big ship made of bread?

Best thing about Charlie?
Similar levels of sarcasm, and our mutual love for Bristol street food chain Chilli Daddy.

Best thing about Allegra?
She employed sarcasm well, and I was inspired to bring forward my next dental appointment.

The shilling for Chilli Daddy is totally baffling (Guardian subs: I’d have hyphenated street-food in this instance) and the obsession with sarcasm – basically banter rebranded, but with wine that costs £8.99 instead of £4.99 – is beginning to wear thin. Much like Charlie’s poor unattended teeth, it would seem.

Would you introduce him to your friends?
I would, but I don’t think they’d have too much to talk about.

“They are all dental extremists.”

Would you introduce her to your friends?
Of course. They might want to see their dental hygienist first, though.

Describe Charlie in three words?
Sweet, sarcastic, quiet.

Sweet, like the packet of M&Ms you eat on the train to being friend-zoned – single journey in every sense of the word.
Sarcastic, like fuck me do these two have any other personality traits other than a yin-yang obsession/aversion to root canal work, the cult of Bristol, and THIS?
Quiet, like I can’t wait for the room to be once I have finished clattering on my keyboard in response to these utter inanities.

Describe Allegra in three words?
Floss. Every. Morning.

What do you think he made of you?
He probably thought I was a bit much. I talked a lot (word-vomited), but mainly because he wasn’t really returning my questions.

OK, so I know we have been giving Allegra and Charlie a ribbing for their one-note chat, but there is nothing worse on a date than someone who does’t ask you questions back. You feel like an investigative reporter, or a… well, a solicitor, which Charlie is training to be. Shouldn’t be be quite good at asking questions? Perhaps they haven’t done that seminar yet. Maybe he was just thinking of his best approach and in a few days Allegra is going to get a really thick case file with all sorts of intriguing conversation points. No idea.

Being with someone who doesn’t found you interesting or fascinating, and has zero curiosity about you, must be very dispiriting. Ask her anything! Do sonic toothbrushes really work?! Was my air-flosser that cost an absolute fortune a waste of money?! Is there any point to toothpaste which claims to restore and repair enamel? See, I’ve thought of three already! (Allegra, please email me with the answers to these questions, thanks.)

What do you think she made of you?
Somewhat charming, somewhat aloof.

That would be a nope. I think we need to look again at Charlie’s first answer here. He “specifically” didn’t want a 20-year-old student and now thinks he came across as “charming and aloof” – which I can only read as “lightly patronising and mute”.

Did you go on somewhere?
No, the night had reached a natural conclusion.

This sounds like a vet pronouncing an elderly spaniel dead.

And… did you kiss?
A kiss was not on the cards. I’m not sure there was attraction on either side.

“He hasn’t been to the dentist in three years.”

And… did you kiss?
I don’t think we had that kind of connection.

“I was worried she was going to shine her phone torch into my mouth and give me a scale and polish.”

Marks out of 10?
A solid 6. It wasn’t bad, but felt like a dinner with one of those friends you don’t know what to say to. (Also, he said he’d follow my food Instagram and didn’t.)

6.

“Hey Siri, show me ‘these two sound like really hard work’. Thank you.”

“He said he’d follow my food Instagram and didn’t” – gosh, I wonder why. Do you think every pic is captioned with the usual blurb about what the dish is, followed by a row of tooth emoji and “Don’t forget to wait at least half an hour after eating this before you clean your teeth!” (Fourth question, Allegra: is that actually a myth? See? This is EASY.)

Also, why are you having dinner with friends you don’t know what to say to? Why are you still friends with them? Ditch!

Would you meet again?
He was really sweet, but it’s going to have to be a no from me. Sorry, Charlie.

A dentist calling you sweet is not a compliment. “He was really sweet, like EVIL TOOTH-DESTROYING SUGAR.”

Would you meet again?
We’re at different stages in our lives, so unfortunately not.

“She goes to the dentist, I don’t.”

• Allegra and Charlie ate at The Kensington Arms, Bristol. Fancy a blind date? Email blind.date@theguardian.com. If you’re looking to meet someone like‑minded, visit soulmates.theguardian.com

NOTE: The comments I make are based on the answers given by the participants. The Guardian chooses what to publish and usually edits answers to make the column work better on the page, but get in touch if you want to give me your side of the story; I’ll happily publish whatever you say. I last went to the dentist in August and required no treatment, thank you.

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