My year in 25 dates

Sex addicts and stuntmen, cool girls and catsuits, married men and an unfortunate attack of indigestion… One writer shares her highs, lows and even lower of looking of love online

One writer’s search for love – via stuntmen, sex addicts and, er, a guy obsessed with Siamese fighting fish

So, is there anyone… special, on the cards?’ We are in my grandmother’s best room. Songs of Praise plays on the television. She pours proper tea from a pot and pats an embroidered cushion on the sofa for me to sit down.

‘There is, actually. I have a girlfriend. Well, a sort-of girlfriend – we haven’t had the talk yet. She’s a lesbian, although I think she prefers “queer”. I guess you could call me “bi”, but I hate labels; I just like who I like. Millennial of me, I know… Anyway, we’re seeing each other, but now she’s trying for a baby with her best friend – a gay man – and I get it because she’s 38 and her eggs won’t last for ever. So yes, I’m in a casual semi-relationship. Or a potential thr-ouple. Or something.’

My grandmother drinks her tea and waits for me to answer. What I actually say is, ‘No, no one special.’ She tells me about a man who runs the youth club at Trinity Baptist; he has a chemistry degree. ‘I’ll get his Hotmail for you.’ I take a big bite of Battenberg.

Until I was 31, I’d only ever dated two people. The first, my best friend Harry, took me to watch Saw II at the Odeon, then to a Pizza Hut, which turned out to be a takeaway joint, so we sat in his Clio in a dark car park, kissing and eating pepperoni pizza. On the drive home he mumbled the word ‘girlfriend’ and that was it, we were in a relationship. We were 18. We lasted 10 years.

After we split (we’d grown apart), I fell giddily for an older gay woman at work who wore ripped Grenson brogues and rode a rusty blue bicycle. I was too besotted to give sexuality much thought. I just loved her, never mind gender. If pressed, I said I was sexually fluid (the only millennial thing about me, since I prefer a night of Scrabble to negronis and once googled the word ‘woke’). The only hiccup was my grandparents, evangelical Christians who consider homosexuality evil. Telling them would risk losing them, so I simply kept those two parts of my life separate.

By the time that second relationship ended, a week after my 31st birthday (because – gulp – she didn’t love me enough), most of my friends had married lovely Home Counties men and accumulated babies, Bugaboos, houses in Hertfordshire, and kitchens stocked with celeriac, spelt bread and eggs from their own chickens. Meet-ups were scheduled months in advance. They hosted actual dinners with napkins.

And so I embarked on a 21st-century dating odyssey alone. Was I too old for Tinder? Should I choose Bumble (where women message first), Happn (based on location), or The Inner Circle (for professionals)? (Turns out hardened singles join them all.) Who messages first, who pays the bill? And what on earth is a ‘catfish’? One year and 25 dates (four women, 21 men) later, I’m finding out.

YODA 1 Met through: work party

He’s six years older than my father. He is a yogi (and millionaire CEO) with tangerine skin, bleached teeth and a six-pack. Last week he went on a healing retreat in Mustique. He invites me to his club for drinks after discovering I’m newly single, but I’m unclear whether it’s a date. I consider asking for clarification, but my single friend looks horrified, then reassures me it will be immediately obvious. It’s not. We discuss the Budget, our poor flirting skills, his famous relatives, his estranged children. He gets tearful. I’m positive we’ve connected and wonder if he’s going to kiss me – but he is staring at a waitress. As he hails me a taxi, he says, ‘Your hot friend from the party, is she married?’ Suddenly I feel stupid. Leave deflated.

CATMAN Met through: Tinder

We meet at his favourite rooftop bar. Everything is chrome and neon and a bit greasy. His cheek is damp when he hugs me hello. He finishes his vodka in one gulp and says his fantasy is to have sex with a woman in a latex jumpsuit. I fiddle with my straw, wondering how to escape, then he takes my glass and drinks from the straw without breaking eye contact. I feel dirty. I tell him I have an early start, I should go. ‘Do you have IBS?’ he says. ‘Most slow drinkers have IBS.’ I say I do and walk out. Later he Whatsapps me a picture of Catwoman. I block him.

GENTLE GIANT Met through: blind date

My friend Lily sets me up with her husband’s friend. He’s blonde, gently spoken and tells me he’s relieved I showed up, as many women don’t. I reply that I’m surprised high-calibre dates like him get stood up, and realise I am accidentally flirting – I didn’t think I knew how. He works as a seating designer and I show him my Pinterest board of inspiring accent chairs. He nods politely. We go to a bar with battered sofas and grapefruit cockails in jars. I’m not a big drinker but these are delicious. They don’t taste alcoholic at all. I drink six and realise he is more attractive than I thought. And is that an emotional bond? Tell him all about my ex-girlfriend, my grandparents’ homophobia… The next day he texts Lily: ‘Is she an alcoholic?’

EMOJI MAN 4 Met through: Tinder

He’s so chiselled. And stubbly. And he is wearing Scandinavian knitwear and writing a children’s book for his disabled niece. Am immediately tongue-tied and limit myself to two small red wines. Before we say goodbye, he pushes me against a wall and kisses me until I am giddy. Later he texts, ‘I knew you’d be a good kisser.’ I’m bursting with excitement but have no idea what to reply… so I don’t. I mustn’t mess this up. I google ‘date etiquette’ and whenever he texts, I wait 36 hours to reply. A single friend commends my discipline. When I finally agree to a second date, he replies, ‘Sorry, started seeing someone.’ I’m supposed to send him a breezy emoji to confirm my nonchalance. Instead I send a text essay explaining at length that I’m newly single, find dating confusing and did, in fact, like him. He replies with a winky face. ‘You snooze you lose.’

MEGAMIND 5 Met through: Tinder

Meet a man with an enormous brain who does something with algorithms for Facebook. Spend half the date in the toilet googling technical terms. Selfishly relieved when moped thieves snatch the handbag of a woman on the next table; I watched a documentary about moped crime and can tell him everything I know. Finally feel intellectually on a par. He suggests we remain friends. Smile, nod and know we never will.

THE MIDWIFE 6 Met through: Tinder

I’m sure we’ve connected and I wonder if he’s going to kiss me. ‘Your hot friend,’ he says, ‘is she married?’

She has short curly hair, strong cheekbones and moth holes in her cardigan, and bicycles around Peckham delivering home births. I ignore the fact she looks like my ex-girlfriend. We chat for hours – about our Scottish upbringings, coming out to her

catholic mother, plays she’s written – and when we look up the bar is closing. Outside I nervously mutter ‘see you’ and scuttle off. Idiot! Immediately text her, ‘Sorry for awkward goodbye. Had fun. Let’s do it again?’ She replies yes and I do a victory dance on the bus. A single friend scolds me for being keen. We set a second date for the following week.

DR KNIEVEL Met through: Tinder

The GP is 5ft 2in, lean and a stunt-performer in his free time. It’s not his lack of height that puts me off but the fact I feel bus-like beside him. He orders chilli-beef nachos. I look at his tiny hips and order cauliflower. He asks me if I’m paleo. I decide he is not my future husband but I’ve pledged to make the most of every date, so I roll up my sleeve. ‘Could you take a look at this mole?’

DIAGNOSIS JAUNDICE Met through: Tinder

He has the pallor of someone who has never been outdoors. He works as a computer programmer. He is faintly yellow. He has zero chat. I leave after a coffee and arrive early at Hampstead ladies’ pond for my next date with the Midwife, our sixth. Try hard to pretend I’m OK with public nudity and pondweed. She says she has something to tell me, and I hope she’s going to ask me to be her girlfriend. She says she is being seconded to a refugee camp in Lebanon.

COCKNEY BALBOA Met through: Tinder

Peanuts and beer with a boxer who is a family friend of the Krays. I tell him I like his Eastenders vibe. He shows me his scars. He’s sweet… but I can’t stop thinking about the Midwife. I also realise I’m not over my ex girlfriend – suspect I started dating too soon. Delete Tinder and take a twomonth dating sabbatical.

JANET Met through: Tinder

Summer. A heatwave. Re-download Tinder, Bumble and The Inner Circle, and schedule back-toback dates. The first has big teeth and talks like Janet Street-porter. She says ‘right’ a lot. There is zero sexual chemistry but I’m excited to learn about her work at the Foreign Office. ‘Top secret, right…’ Her voice is flat. She fills silences with unprompted statements like, ‘Right, I hope you’re not one of those who eats baked beans.’

SCARY SPICE Met through: Bumble

She has a raspy Scouse accent, a smoker’s cough and pointed fingernails. She is terrifying. Her profile says she’s 38. If she’s under 48, I’d be surprised. Decide not to challenge her.

THE MANSPLAINER Met through: Tinder

He suggests meeting at Tiger Tiger. The last time I went to this sticky-floored nightclub, I was 17 and drank two buckets of woo-woo (a hideous sugary cocktail), but I give him the benefit of the doubt. He tells me that he was recently made director of a telemarketing agency and jabs his finger while explaining that to get promoted I need to ‘work smart, not hard’. He uses the phrase ‘circle back’ frequently and without irony. After one woo-woo (when in Rome…), I tell him I should go. He shrugs and orders himself another.

BIG… BUCKS Met through: Bumble

Start judging people on date venues they suggest. A Canadian businessman invites me for spontaneous drinks at The Connaught. I’m starving and dreaming of an early night but my single friend advises, ‘Just get a bar snack before he arrives.’ I order a samosa and a martini, then he texts: ‘Meet me in my room.’ I tell him I’m more comfortable in the bar. ‘I’m kind of a big deal so you’d better come up.’ I ask him what ‘big deal’ means. ‘Is $56 million enough for you?’ Eat my samosa alone, pay the £34 bill and go home.

SEXAHOLIC Met through: Tinder

The playwright is definitely a sex addict. We meet at Gail’s Bakery, where he vets ‘potentials’. He says he sleeps with 15 women a month, is that OK with me? His voice is incredibly sexy, the way he says ‘Nietzsche’ makes me shiver. Decide to have sex with him; it’s been a while. Back at his Chelsea town house, he prepares some lapsang souchong, then licks my face. Like, wipes off the foundation with his tongue, as I stand there, fully clothed and confused. Afterwards he, erm, takes charge. I leave in an Uber feeling odd but conclude it was a Sunday well spent. The next day he texts, ‘Why haven’t you messaged?’ He telephones at lunchtime and says, ‘I feel like I’ve been emotionally raped.’ I don’t know what to think, so suggest we go on a proper date. ‘But I didn’t think you liked me?’ he replies. I tell him I think he’s intelligent and attractive, so let’s have dinner. He sighs deeply. ‘I told you I’m not looking for commitment.’ We never meet again but he occasionally texts me an emoji to articulate his mood. I always reply, ‘Are you OK?’ but never hear anything more. I feel strangely protective of him.

THE SINGER Met through: Tinder

Give casual sex another go, this time with a female singer in an unsigned band. In her music video, she sits in a car park surrounded by recycling bags, weeping. She is most definitely ‘woke’. We meet at a whisky bar. Her voice is exquisitely gravelly as she talks me through her 26 tattoos. I wish I hadn’t worn loafers. I pay for all drinks. And for the taxi back to mine. Next morning, I need to go to work but she wants a lie-in, so I shrug, ‘Cool, let yourself out.’ Mid-morning panic: I’m definitely being burgled. Hurry home and find that she has made my bed, stacked my dishwasher and folded my discarded clothes. Decide casual sex isn’t for me.

We meet at Gail’s Bakery, where he vets ‘potentials’. He says he sleeps with 15 women a month, is that OK?

MR ‘PERFECT’ 16 Met through: Tinder

We establish that our grandparents live in the same cul-de-sac and we toast what a small world it is. He is exciting but cosy, almost husband-y. In the toilet, I text Lily a thumbs-up. But back at the table he has paid the bill and is ordering an Uber. ‘Work calls.’ He actually runs away. I google him and discover he has a wife and two daughters. His Justgiving page says he had a third daughter who died recently. Feel sad. Go home and eat a familysized Galaxy.

WALLFLOWER 17 Met through: Tinder

A sweet (male) gardening journalist invites me to watch Britain’s Got Talent live. Run out of chat before we reach our seats. The show lasts three hours. There is no bar. Amuse myself by wondering whether Amanda Holden is wearing a wig.

ANTI-BANTER 18 Met through: Bumble

Another journalist; this one works for a slick men’s magazine. He has yellow teeth. Suspect he usually dates models. After one drink he tells me he has a feature to write on deadline. I grin and say, ‘I’ve used that one before.’ He doesn’t laugh.

CASPER 19 Met through: Bumble

The architect is so beautiful he looks airbrushed. Definitely out of my league. But he invites me on a second date. Six hours into it (after brunch, Bloody Marys, wine) we’re kissing aggressively in a ping-pong bar. He whispers I should come back to his. I’ve terrible indigestion and say ‘next time’, in what I hope is a suggestive way. I leave smitten. He ghosts me. Later I recount this to my married friends and ham up the bit about indigestion. They crack up and so do I… but deep down I’m tired of turning bad dates into anecdotes to amuse others. Resolve to remain upbeat but also to be honest with friends – dating is exhausting and the sheer volume of rejection chips away at you.

DANGEROUS LIAISON 20 Met through: Tinder

Strain a leg muscle and hobble to the bar, dosed up on codeine. Fortunately, he is understanding; recently divorced, newly redundant, but witty and charming. He rubs my sore leg and I surprise myself by letting him. After two small glasses of wine, everything is spinning. In the toilet I phone Lily, mortified that I’m so drunk. ‘Get out of there,’ she says. ‘Something’s not right.’ Back at the table, I can’t see my date, then spot him through the window with a man in a leather jacket. By the time I get outside, I need to be sick. Fall into a taxi and pass out at home. Next morning, I’m disgusted at myself – but surely the codeine couldn’t have made me that drunk? Grab my phone to apologise and find 14 new messages. ‘F—ing bitch.’ ‘Bet u went n f—ed sum1 didnt u.’ ‘See u in the next life whore.’ Report him to Tinder. Shaken. Confused. Appalled at his grammar. Tell my younger sister, who gets upset and makes me promise to be safer.

SHY GUY 21 Met through: Bumble

I arrive late and find him finishing The Handmaid’s Tale. Instantly adore him. We have everything in common and can’t stop chatting – seven dates later we still are. We go sofa shopping, to pub quizzes, he meets my friends and fixes my washing machine. And yet… something is lacking. We barely kiss, and haven’t progressed beyond. ‘You’ll have to seduce him,’ says Lily. ‘Make or break.’ I do it that night. He is enthusiastic in principle but lies there silent and static, encouraging me to take charge. Afterwards I stroke his shoulder, not meeting his eye, while he opens up about his sexual history, which is sparse and pedestrian but includes an accident that resulted in him going to A&E. He tells me he’s a lapsed Christian and was a virgin until last year. I feel for him... but his passivity has killed any last jot of passion I’d felt. Leave it a week then suggest we revert to being friends. He agrees. A few weeks later he tells me he is dating a fierce and notable FGM campaigner. ‘She’s amazing. I like strong women,’ he admits.

SOMETHING FISHY 22 Met through: Bumble

The psychotherapist talks a lot about his Siamese fighting fish called Steve. He invites me back to his flat to meet Steve. I politely decline. He has murderous eyes.

CASANOVA 23 Met through: Bumble

The Italian takes me to an underground bar in Soho and doesn’t judge me when I ask if the Mafia operates in Sardinia. His answer is fascinating but I only decipher half beneath his accent. At the station, he asks to kiss me and I feel guilty suddenly. ‘Your heart is with somewhere else,’ he observes, before I can answer. I nod. The Midwife returned from Lebanon a few weeks ago. We’ve since been on six more dates and though I’ve deliberately kept it casual – I can’t imagine living in her damp, subsiding flat or marrying a person who wears moth-nibbled cardigans – I can’t bring myself to kiss someone else. ‘You should try for love with this person,’ says the Sardinian. I thank him for being understanding and set him up with a friend.

NAUGHTY NEIGHBOUR 24 Lives next door

This is not supposed to be a date. My neighbour invites me to the pub. When I arrive he hands me a rose, grips my arm and says, ‘I have a wife in Lahore but I’m single.’ I go to the bar to compose myself – he asks for a Smirnoff Ice. I text the Midwife about my peculiar evening. She replies at length: she has loved dating me and doesn’t want it to end, but after serious deliberation she has decided to have a baby with her best friend. She’s 38 and doesn’t want to leave it too late. She hopes I understand. I go home and cry.

THE MIDWIFE: PART 2 25

Christmas. Shy Guy (date 21) is single again and sends a cheery festive text. My grandmother spots the message and asks who he is. I share the PG version and show her his photograph. ‘A young Brad Pitt!’ she squeals (she also called my ex-boyfriend this). She suggests I give him another bash. I nod – but I’m still thinking about the Midwife. Lily tells me about a lesbian couple she knows, one of whom was older and pregnant when they met. Now their son is nine and they’re happy. I say, ‘But isn’t it weird the Midwife looks like my ex?’ Lily laughs and congratulates me for finally discovering I do actually have a ‘type’: tall, gutsy, creative lesbians with dark hair, strong cheekbones and bicycles. I give it some thought. A few weeks later, I arrange to meet the Midwife. It’s early January, frosty. She wears her motheaten cardigan; suddenly I love that it’s familiar and smells of her. I blurt out that I’m sorry I was acting too casual and, ‘I know it’s complicated but I really like you… Let’s give it a go?’

He invites me back to his flat to meet Steve the Siamese fighting fish. I politely decline