I once dated a man who told me he lived in Marlborough. It turned out that he lived in his car, which was parked in Marlborough. This story pretty much sums up my colourful dating history, which started when I got my first boyfriend at 16. He was a wannabe firefighter in the year above me at school, and was a perfect first in every way, but he also became the first boy I lived with. He moved into my parents’ house when his own family situation became untenable and I got very used to going to bed next to someone every night.
That’s probably why I spent the next decade as a serial monogamist, hopscotching between men. The only thing they had in common was that they were always older. They were fellow journalists, personal trainers, photographers, chefs, finance boys and musicians. After sixth form, and then university, I met most of them at work in London, where I had an office and colleagues, plus after-work drinks at the packed pubs opposite.
Later, freelance life was solitary but global and I went to as many events as possible: new people were my drug. I hadn’t realised yet that I just didn’t know how to be alone. Anxiety raged in the London rat race, and men and booze had become props. Despite having parents still married (now for 34 years), I couldn’t settle on anyone, anywhere.
At 26, I met a girl, and moved in with her, and then met a guy and had the worst relationship of my life – fleeing London and him at the beginning of the pandemic and wondering, in my teenage bedroom at my parents’ house in Bath, whether I’d ever meet anybody ever again. When the world opened back up I started writing a dating column and really went for it, adding younger men, women and polyamory to the mix.
Now 34, I’ve tried pretty much every way to meet someone there is. I’ve got six dating apps on my phone, been to retro singles nights, Twister dating events at the top of the Shard, Brexit speed-dating in Birmingham, attached a “single ring” to my hand to make it obvious I can be chatted up, and even moved country with the secondary aim of meeting someone more easily. I now live in Glasgow, having realised I knew everyone – and their dating histories – in Bath. I didn’t find it difficult to meet someone IRL, but it was hard to find a keeper.
The dating app Badoo found recently that three in four singles have deleted a dating app profile, with almost 40% saying they had lost confidence that people were who they portrayed themselves to be online. A quarter felt burnt out from dating.
So what about going back to basics and trying matchmaking (something Tinder even has a new feature for)? What if meeting someone wasn’t down to me at all? I asked nine very different people in my life to set me up. This is what happened.
The dating professional
Martine, 57, London
The setup
Martine Davis runs the dating agency Page Introductions single-handedly, via a little book of contacts. With a dating column for the Jewish Times and a successful marriage behind her, she turned her hand to bespoke setups that begin with a six-page questionnaire. Biographical details (the usual, plus things like “Am I attractive?”, “Do I own a home?”, “What books/films do I like?”). Then there’s an informal interview in which we talk about men, and laugh for an hour. (Martine once ordered a ham pizza to put off a very boring Jewish date, so she’s got wisdom to share.)
Matchmaking works, she says, because she can ask questions the dater can’t. “It’s hard to dive into whether someone wants kids or wants to settle down if you meet in a bar – but I can ask everything for you.”
At lunch, Martine puts three dates in a leather-bound notebook and promises to send a summary of each that night. The first guy, an ex-army type in his 40s, says he would love to meet but is about to leave the country on a lads’ trip to Africa. The second leaves a voice note and – seemingly forgetting he’s doing that – lets off a long fart halfway through. Right, I think, who’s the third man?
The date
Two weeks later, I’m waiting at an outside table at a bar in Paddington in west London for Riz, having only seen a headshot and trying not to drink the wine I’ve ordered too quickly (nerves). Almost no back and forth on text makes me feel like it’s all to play for, and I’ve got nothing to lose. It’s refreshing.
When he walks in, I notice that he’s tall, attractive and smells like aftershave in the triple-figure price bracket. He’s also a lot older. (Did I mention using Page starts at £4,750 for six months?)
He offers me a drink and goes to the bar, and I try to imagine us together. Would I also have to start wearing a lot of linen, I wonder? Would I get expensive perfume for Christmas?
This turns out to be the date with the least chemistry. Maybe that’s because he spends the first 20 minutes showing me videos of a protest on his phone “proving” that all journalism is disinformation, or because he works in some techy-finance thing that I’d never be able to get my head around. He’s a nice guy with superb manners, but a spark? No. The most fun thing about it is calling Martine afterwards, knowing that she can ring him and get the lowdown without me having to send any kind of follow-up text to him.
“Do you want to go back to The Farter?” Martine asks.
First impressions?
Very suave, probably quite rich, bit too serious, age difference too stark.
Would you meet again?
Nice man, but what would be the point?
Marks out of 10 5
The stranger
Stephen, 42, Glasgow
The setup
It’s late one Thursday night and I’m at the pub with my friend Sam when a smart, dark-haired man approaches and asks if I’m single. “Old-school come-ons aren’t dead!” I think, before he explains he comperes an improv, blind-dating comedy show called Looking for Laughs and would love me to come on. It’s filmed in front of a live audience, he adds. I’m terrified by the idea. “Did I mention you get £30 and free drinks?” he asks. “You did not,” I say.
The date
I’m sitting in the “green room” ( freezing-cold smoking area) of the Van Winkle pub in Glasgow, drinking a bottle of prosecco and lighting another cigarette, having quit a month ago. Stephen appears with an eye-mask, which I’m supposed to wear for the first half of the hour-long show.
By the end of the first half, I’d rather not take it off. My first date (let’s call him Kev) may or may not have dropped a class A or two before he got on stage. This is a guy who seems not to like women being funnier than he is and his jokes turn sexist fast. The improv performers – who take the mickey out of the date at half-time – reassure me that it clearly is as bad a date as I’d thought.
When we remove our blindfolds, “Kev” is revealed to be quite attractive, and I congratulate myself on being far less shallow than I thought I was – no amount of good looks can make up for his personality. “That was bonkers,” concludes Stephen, whose own highlight is the moment I ask the audience if anyone else would date this man, and tumbleweed rolls.
First impressions?
Misogynist, probably off his face.
Would you meet again?
No.
Marks out of 10 1
The new friend
Claire, 36, Glasgow
The setup
Claire and I were practically set up ourselves; I’d been living in Glasgow for about two months when a friend introduced us at a party. Soon enough, Claire suggested that I meet Pete. They had already dated (10 years previously), but maybe that’s why she knew we’d get on. Several months after she first introduced us, we go to the pub.
The date
I decide to wear a new blue top with a cherry design, and it keeps falling down. He tries, awkwardly, not to look. I refer to this being “our first date” and he practically falls off his chair. “Just kidding,” I say, thinking, “Shit, is this not a date?” We have a few pints, then move on to a wine bar down the street. He’s so difficult to read. I find myself becoming more flirtatious in an attempt to prompt something. But he’s very attentive, he has style and there’s something about him I definitely like. I’m pretty sure we don’t look like we suit each other but there’s chemistry. Maybe too much. The night ends in a slightly drunken row over something I can’t even remember.
First impressions?
Enigmatic, funny, distanced.
Would you meet again?
Yes … as friends.
Marks out of 10 8 (despite the row)
The old friend
Serena, 33, Jersey
The setup
Serena, who I’ve known since sixth form in Bath, deems the chance to flick through my Feeld (a sex-positive dating app) on a Sunday night in Jersey a great activity. Serena is one of my oldest friends but she’s at a different life stage – married with a daughter, and about to give birth again. (She’s also the former captain of the England netball team.)
Given Serena and Bob have been together for seven years, her experience with the apps is limited.
“I’ve gone through your cards quickly,” she says cutely, meaning the profiles. “It made me feel like we should have spoken years ago about what you’re looking for, because I realised I didn’t have a clue.”
Serena finds me three options – two with a comedic edge, she explains, and one who looks very active. “You can go for dinner with anyone,” she says. “I think we need someone who thinks outside the box for date one.” When I check the matches on my phone, I’ve got a very attractive scaffolder in an array of questionable T-shirts; a surfing writer with bird’s-nest hair who wants a travel buddy; and a gym-heavy Scorpio who seems very impressed that he’s just done Hyrox (the weekend exercise festival thing). There’s also a toothy colonel in his late 60s. I need to amend my settings.
The date
I decide to message the surfer, thinking we’ll at least be able to talk about writing. He suggests mini-golf for a first date (my head slams into my laptop keys). I suggest darts and he says he’s having time away from pubs (equally worrying). We settle on a walk around Glasgow’s Pollok park. I’m reminded of pandemic dating, when it was hard to vibe with someone when you had to turn your head to look at them from the side. We shake hands when parting and I wonder whether I can message the scaffolder without being flooded with dick pics. He looks the type.
First impressions?
Stoner-type, shorter than me, a latte-drinker (the cop-out of coffees).
Would you meet again?
Possibly, if I smoked weed.
Marks out of 10 4
The gen Z-er
Leah, 24, London
The setup
“I met my boyfriend in a bar and we didn’t leave each other for a week,” Leah grins. We’re at her older sister’s – my best friend’s – baby shower and it strikes me that, given she’s still with the same man two years later, she must be able to spot a keeper. The problem is that she’s in London and I’m in Glasgow, so we have to do it online. Most of Leah’s friends are on Bumble, so we decide to use that app, and she logs on to my account from London to pick my match. It’s at this point that I remember that Leah is far cooler than me. The man she chooses is much more attractive than the type I usually go for (I don’t usually trust model looks): a 6ft 4in frontman of a band.
The date
The musician decides that we should meet at a bar near my flat, so I don’t have to travel far. Considerate all round. The problems start when I can’t clock off work on time and text to apologise, profusely, that I’ll be half an hour late. “That’s fine, no worries,” he replies. Then I arrive to find he’s ordered and eaten without me. “Chip?” he says, offering me the dregs of his dinner.
Possibly this is all I needed to know but I still feel I owe him for being late, so I tell him there’s wine in my fridge if he’d like a drink after the pub, which is calling last orders. At my flat, he suggests playing his own music. He made a “visual album” (ie YouTube video) in lockdown. He puts it on my TV. I would describe it as … not really my kind of thing. Each song is followed by a clip of him riding a bicycle or standing by a gate talking about how he’s depressed because it’s lockdown. I decide one date is enough.
First impressions?
Tall, handsome, far too serious.
Would you meet again?
Would say hello if I bumped into him.
Marks out of 10 4
The smug marrieds
Hermione, 33, and Greg, 35, Inverness
The setup
“Oh my God, we’ll set you up!” says Hermione, my boss at the Aigas Field Centre in Beauly, where I’m learning what it takes to become a highlands ranger. With much excitement, Hermione starts assessing her contacts, and realises that it’s harder than it seems. Then she has a brainwave: Joe, a fellow writer who lives in Edinburgh and wants to know whether I’ll buy him dinner.
“Let me check him out first,” I tell her, wondering if the guy is tight, broke or a diehard feminist. Turns out he’s tall, dark and handsome.
“Go on then,” I say.
The date
Hermione tells Joe I’m keen, and we wait. And wait. And wait. “I’ve sent him three texts,” she messages me. “Shall I text him again?” she asks.
“Ahhhhh, I know what’s happening,” I inform her. “He’s ghosting me, via you.”
“WHAT?” she says, really quite pissed off. This is her first ghosting. “We’ve been ghosted,” she tells her husband.
“Bastard!” says Greg.
First impressions?
Caspar the unfriendly ghost.
Would you meet again?
No.
Marks out of 10 0
The ex
Meg, 34, Texas
The setup
“I’m a lesbian, right, so the hardest part of this is picking someone for you, not me,” says Meg. She’s my only female ex; the first and (still) only girl I have dated seriously.
We met via a netball team in Regent’s Park, London (both looking to make new friends), when we were 29 and had both only dated men until then. Quickly, we saw “us” as something inevitable; different from anything we’d had before. Meg made me wonder whether gender trumped everything in relation to love. But 10 months after we met, her visa ran out and I didn’t know what I’d do without her in my life.
The date
“What the hell, Meg?” I ask, when I see her top two choices on Hinge. “I mean – have I ever gone for anyone like these two before?” She’s opted for profiles I never would have chosen – ones that start with “Would you rather … ?” questions, as though dating were a pub quiz. I open up a conversation with Ewan, who works in a school and looks “very fun”, Meg assures me. She has also put on my profile that I’m letting her set me up, so he must be game. “What’s your biggest ick in men?” Ewan asks. “Can I say use of the word ‘ick’?” I ask him. The conversation fizzles fast.
I decide to invite the female match, Kerry, for lunch and we meet at a ramen place in the West End of Glasgow. She is nice but, weirdly, looks like Meg. Has Meg picked herself? Plus the girl seems to be confused by the setup and is wondering if she’s been catfished. I’m right here, I think, wondering if she’s also failing to feel any chemistry. It reminds me of the difficult conversations I have with chatty cab drivers when I’m in the back, hungover.
First impressions?
Too much of a closed book.
Would you meet again?
No.
Marks out of 10 3
The mother
Caroline, 70, Bath
The setup
My mum agrees to take over my Tinder via the app’s new “matchmaking” add-on. You give your trusted matchmaker access to profiles you would normally scroll through yourself, so they can vet them.
The date
“I didn’t realise it was so hard to find someone normal online,” my mum announces after scrolling. Reasons for rejection include: “Teeth too white”, “Blingy earrings”, “Too smooth in his too-white trousers” and “Absolutely not, because he clearly lives in the gym”. She perseveres with staunch maternal ambition, telling me “someone at work managed to meet an autistic stonemason on Tinder”.
Finally, she finds “the Biker”. I presume she hasn’t seen the motorbike in his second picture because no mother wants this. He looks very nice – maybe too nice. “It’s time for someone nice now,” she says, reminding me that “nice doesn’t have to mean boring”.
I’m not so sure, until I meet him and it turns out we’ve already met. He’s a barman who served Pete and me on date number three. We meet in a wine bar local to both of us, and he stands up when I arrive, asks what I’d like to drink, walks me home. An old-school gentleman type. Maybe that’s because he’s a former military officer.
Then – stupidly – I didn’t follow up very quickly. “Could I really date someone my mum had chosen for me?” I wondered, fighting parental control like a teenager. Luckily, I gave myself a pep talk, because the second date was even better. And the third was even better than that. He kept coming back, and I found I kept wanting to let someone in. Finally.
First impressions?
Beardily attractive, great manners, a gentleman.
Would you meet again?
We’ve just got back from our first holiday. Success!
Marks out of 10 9.
Some names and details have been changed.