He helped rewrite the copy so that I sounded more fun, though not as fun as Jack wanted me to sound. There was an immediate response in the inbox. ‘Reading between the lines, I think you’re holding out for something unusual,’ one said. ‘I believe I’m atypical. For a start I don’t have a television. When I had one I spent a lot of time shouting at it.’ I replied that I couldn’t bear to watch Question Time either. ‘No, no,’ he said. ‘Countryfile, for instance. Countryfile’s really annoying.’ I asked him what he did in the evenings. He said he spent a lot of time with his lizards.

It was a grim Tuesday night, the rain lashing down. I went in search of someone friendlier. There were lots of men who claimed to be the life and soul of the party, but who looked like serial killers on Wanted posters. In general, using a bad passport photograph to illustrate your page isn’t the best of all possible plans. I rummaged through the first five candidates the system had offered and had a look at what they had to say. ‘Scientific facts are never true. If you know why scientific facts are never true, you might be the girl for me.’ ‘Still looking for the right one, a woman who won’t expect me to be at her beck and call.’ ‘Second hand male, in fairly good condition despite last careless owner.’ ‘I am a complex person, too complex to explain here, a hundred different men in one. If you want a dull life you are wasting your time. Move along – nothing to see here.’ ‘Looking for intelligence, co-operation and a natural blonde.’ (Co-operation?)

Perhaps, I thought, I should narrow the search, by ticking some of the boxes for interests. A search based on ticking ‘Current Affairs’ brought up a raft of virtue-signallers. ‘I’m dedicated to the pursuit of justice for all and hate political unfairness.’ ‘The top three things I hate are liars, deceit and war.’ (Whereas, presumably, the rest of us are assumed to approve of wars and lying.) Then I had a brief conversation with a man who said he loved world cinema. I messaged him asking what kind of films he liked. Back came the reply: ‘Hi thanks for asking, my favourite movies are Driller Killer, The Lair of the White Worm, Cannibal Holocaust, I Spit on Your Grave, Cabaret and The Blood-Spattered Bride.’

The first dinner offer came from Trevor, an American expat in London. Trevor had been dumped and was only just passing out of denial and into acceptance, he said. He was doing the work (the therapeutic work on himself, he meant), but was finding it hard. Four thousand words of backstory followed this statement, and in return, I gave him mine. A few hours after this another great long email arrived, talking philosophically about life and quoting writers. It was charming, endearing; I reciprocated with my own thoughts, quoting other writers. We were all set. Then, the day before dinner, Trevor cancelled. The last line of his message said: ‘To be honest, I’m not interested in a woman who’s my intellectual equal.’ (I know this sounds as if it might not be true, but I’m sorry to tell you that it is.) He added that he felt honesty was the best policy. I didn’t like to tell him what my policy was, but right then and there it could easily have involved a plank, a pirate ship, a shark-infested sea and a long pointy stick.

The first real-world meeting was for a coffee in town in the afternoon with an HR manager, between his meetings: a short, sharp interview that I failed. I didn’t mind too much. He was pursed-mouthed, unforthcoming, with dyed black hair and the demeanour of a vampire. Determined to exorcise the bad first date, I agreed to another, with an apparently jaunty tax specialist. Ahead of me in the queue, he bought only his own cappuccino and cake, leaving me to get mine, and then for twenty minutes I heard all about the many, many times he’d seen U2, told one concert at a time. By then my cup was empty. In all sorts of ways my cup seemed to be empty.

It wasn’t just the bad dates that were ending badly. I had a good date that also ended badly: a success so tremendous – dinner that led into dancing, and after that a walk by the river, and then a glorious snog – that I couldn’t sleep afterwards, but lay awake imagining our life together, a fantasy outcome put to an end by his cutting me dead. Sometimes people have one great date with someone and that’s enough for them. A series of great first dates is all they’re hoping for; that’s all they need. I hadn’t anticipated this, not anything like this. I came from a much more straightforward, more traditional dating culture in which people got together at discos and parties and via friends of friends, and stayed together for a long time. We were open with one another, back then, and love was fairly simple.

I decided that what I’d do was establish a real friendship with men, over email and text and sometimes even over the phone (I’ve never liked the phone), before agreeing to meet them. Talking people into being interested in you before meeting – that’s where you might expect the internet to excel. That could be a process designed to work in a middle-aged woman’s favour, circumventing the shock of her physical self when a man met her in person. Undeniably, I had been a shock to some men I’d met, and I wasn’t the only one to have had that experience (look, I’m not particularly hideous). I’d been talking to other women of around my age who had found the very same. It was agreed that there were notable (noble) exceptions, but in general men had expectations that a woman who’d ‘put herself out there’ would dedicate time, effort and money to her appearance, so as to compete. Some men are of the opinion that the whole physical manifestation of a woman on the earth should amount to an A–Z of efforts to please, and that we’re all madly in competition with one another. There are men who think that’s all that lipstick means. There are tabloid newspapers that suggest that’s all that clothes mean, and who divide women into goat and sheep camps, the frumpy and those who flaunt themselves. There have been men, in the course of this quest, who have been openly scandalised about my lack of commitment to looking younger. But then as Jack kept telling me, ‘Men are visual creatures.’ He was doubtful about the Scheherazade strategy, one involving telling stories and general email-based bewitchment. Nonetheless, I resolved to stick with plan A. I decided that I would be quirky, and bright, and a little bit alpha, and I was going to be my real age, for as long as it took. Initial disappointments wouldn’t deter me. I was going to beat the system and find the man I’d want to be with for the rest of my life. I was just hoping it wouldn’t take another 1001 nights.

Trying to Write the Right Profile

Here’s my first attempt at a dating profile. The additions in bold in brackets are my reactions to reading it now.

ABOUT ME

Tall, dark, reasonably handsome woman, just turned 50, hoping for second love after the end of a long marriage. (Is tall, dark and handsome a bit of a macho way to introduce yourself? I’m trying for witty, but I think I’m just coming off as annoying, to misquote Rex the dinosaur in Toy Story.) Intelligent, lively, curious, bookish. Not a skinny person. I’m just saying. Not obese either, but if slender is your type, then I might literally be too much to handle. (Christ, no, that’s not even funny.)

WHAT I’M LOOKING FOR

A tall, clever, funny, loyal, lovely man. (Not much to ask, is it?) Ideally, someone to grow old with. Someone bookish, good-humoured, sociable, kind. (You should probably have written: ‘Happiness; not interested in flings’. That’s probably enough.) I have a bit of a thing for big sturdy academics who rock a linen jacket. (Oh no.)

MUSIC

My music likes are catholic, as in wide-ranging and not as in Vatican City. (You’ve just offended somebody.) Jimi Hendrix, Kathleen Ferrier, Pat Metheny, Philip Glass, Rolling Stones, Talking Heads and all the usual classical. Not really an opera person. Fond of seventies and eighties tracks that remind me of being a student. Neil Young, Joni Mitchell, Glen Campbell, Velvet Underground, John Martyn, Blue Nile, Marvin Gaye, Blondie, Pretenders, The Cure, David Bowie. Very fond of wordless film scores and ambient. Favourite guilty secret: Fleetwood Mac. (Accurate enough, though you’ve completely omitted the jazz you listen to all day. And I’m not really sure why you’ve written all this.)

BOOKS

Usually have a book stuck to my face. British and American nineteenth and twentieth centuries, and the usual retinue of greatness: Dickens, Austen, Brontë, Wharton, James. Oh, and those Russian chaps, and those French chaps (that you don’t read much. Plus, your cuteness is already annoying). Currently on the bedside: Michel Faber, Richard Ford, Kazuo Ishiguro, Fitzgerald, Franzen, Forster, Iris Murdoch. Larkin and Eliot. Art books. A.N. Wilson’s The Victorians. (This is true but you might be trying too hard. Perfectly nice men who read only 99p Kindle thrillers will be deterred. It doesn’t matter what you read or what other people read.)

FILMS

Twelve random Desert Island films: Local Hero, Some Like It Hot, Philadelphia Story, Annie Hall, Hero, Blazing Saddles, Two Days in Paris, Stranger than Fiction, Rocky Horror, Monsieur Hulot’s Holiday, A Night at the Opera, All About My Mother, Blade Runner. (Except that’s thirteen.) I’m a big fan of world cinema of all sorts. Guilty pleasures: The Bourne franchise, popcorn thrillers.

FOOD

Basically Nigella. (You are embarrassing.) Very greedy and eat almost anything (you’re saying you’re fat). Cooking and eating are important, as you will see immediately you meet me. (You keep telling the boys that you’re fat, you know.) World food rather than just traditional British, though in reality there’s a lot of chicken. In summer, fish and chips out of the paper while sitting on a sea wall. Restaurant pick for a blowout dinner – mussels to start, venison or duck, lots of cheese, a clever chocolate pudding. And wine. Lots of wine. Garlic with everything except custard. Death Row meal: steak and sweet potato fries. (Really not clear why you’ve written down any of this.)

ART

I’m an art nut and go to galleries a lot. I have trouble with some of the conceptual stuff but am not completely ungroovy. (Oh God.) I’ve even admired the occasional video installation. I like primitive art, Renaissance art, nineteenth-century art, early/mid twentieth-century modernism. I like abstraction, colour, some expressive work. Howard Hodgkin. (At this point you’ve probably deterred people who think this is a spec, rather than just your own ramblings.)

HOME

Home means a lot, physically and as an idea. I like to decorate, in different senses of the word. (No, me neither.) Having said that, heading off with a rucksack and being forced to be a world citizen would probably be good for me. At home I feel the pull between sleek functionality and a more cluttered, wildly coloured nineteenth-century approach with some Moroccan-boho touches. (A chap might wonder if you’re asking to be housed and to be given a furnishing budget, at this point.)

TV AND RADIO

Radio 3 and 4. Not a live-TV watcher, in general. Low tolerance for commercials. No tolerance for reality television, of any sort. I like thrillers, crime, suspense, psychological. Quite partial to the occasional bonnet drama (I don’t mean cars). Culture and science docs. (You sound like a media snob. But that is accurate enough.)

PLACES

I haven’t been to enough places. I know bits of Europe well and tend to return to them. Ideal holiday: a place with swimming plus exploring opportunities, interleaving history/travel days with relaxing days. Wild swimming fan: lakes and rivers often preferred to beaches. No interest in the Caribbean or tanning. I want to see more of the world. (Add that trekking in Nepal and Machu Picchu are not on the list.) I want to see ‘Arabia’ as the nineteenth-century explorers saw it. (Do not say this – people will delight in misunderstanding it.)

POLITICS

Sensible-compassionate left-middle. (Don’t use the word compassionate about yourself. Or charismatic, come to that.)

SPORT

No. Unless you count walking the dog. Or watching Wimbledon and Six Nations rugby. On the television. On the couch. (This is brave, perhaps, but necessary. Too many midlife men are gym-oriented.) I cycle, but rarely uphill.

WEEKENDS

An ideal weekend: eating, reading, going out for a mooch and a coffee, dipping into a museum, going to the cinema, making dinner and drinking wine. Or: off to a wild green place for walking and the pub. Or: gardens and NT houses with tearooms. Weekends away in B&Bs. Walks on the beach in winter. (Beaches in winter are a total dating cliché.)

What I think when I read this over now is: I wonder how many people thought they wouldn’t fit the bill, because they watched, read or did the wrong things, and because they interpreted a detailed account of myself as an equally detailed wish list. In a way this can’t be helped: the whole point is to give an idea of what you’re like and how you tick. It’s very difficult to get it right. Some of the reactions I had to this first attempt were, ‘Well, you’re not expecting a lot, are you?’ (sarcasm) and, ‘You come over as a smug middle-class bitch.’ But, you see, I wasn’t interested in the sort of men who would write to women to tell them that. So, perhaps, although some of the above is cringe-worthy, it’s on the right tack, in being personal, at least. Smugly middle class and with high expectations, maybe – but personal, at least.

First Bites and Backbites

SPRING, YEAR ONE

So, the plan was to make a man fall a little bit in love with me by email before we met. The idea was that this would make me feel less nervous about meeting a stranger.

The project didn’t start well. The first attempt was utterly doomed, because the man in question wasn’t a communicator. To Ralph, texting was for making social arrangements, and emailing was for making more long-winded social arrangements, and he didn’t grasp that both could be used as a form of foreplay. I’m not saying this was a bad thing, per se. Each to their own. But yes, Ralph and I were a mismatch, in this and in other ways. I persisted, though, for five weeks and seven dates, because he was an incredible kisser. We’re talking world-class osculation. It was the kind of kissing that could turn a person’s head and make them conclude, totally wrongly, that a lifetime of bliss lay ahead. Sex (sixth and seventh dates) was a complete disaster, though. I don’t mean that the mechanics of it were a failure, despite the fact that I was undoubtedly a nervous wreck. It was just unsexy: weirdly, profoundly unsexy for both of us. It was odd. The kissing was our sex. The kissing was as erotic as hell. The sex, however, was more like shaking hands with your bottom.

I did wonder if Ralph had an aversion to body hair. There were men, in this story, who were enthusiastic about ‘a seventies vibe’ and there were men who had to stifle a shriek. There was a man who asked, flat out (via the messaging system) if I shaved, and who was angered by my response; my having pubic hair of any kind was rude to him, he thought, like being unshowered. The best sort of men are those who don’t give a shit how much hair you have, or where. (Listen, chaps – try having your pubes ripped out with hot wax, on a regular ‘maintenance’ basis, before declaring a preference.)

So, things didn’t work out with Ralph. For him, perhaps it was that I didn’t have the pudendum of a 10-year-old girl. For me, it was his lack of interest in talking when we were apart that killed the urge to keep trying. He was perfectly friendly when we were face to face, but terse or silent between dates. A goldfish, in online dating terms. Often he ignored texts and emails, and if he replied at all it was usually three words, using his catchphrase: ‘Catch you later!’ I sent him an email one night telling him about a bad day, and his reply was: ‘Looking forward to catching you soon!’ I’m sorry if this sounds needy, but I needed more. Six words seemed like they might indicate a lack of interest.

Not that I could make claims to be the norm from which Ralph was deviating. Ralph had no way of knowing that I was emotionally rather catlike in needing frequent small meals of love. He had unwittingly stepped into a game in which he wasn’t really aware of the rules. I texted him after date number six, asking if we were still on for Friday. ‘Yes! Looking forward to catching up with you!’ the reply said. He’d signed it with his full name, including his surname. Who writes their surname on a text? Did he think I’d need to distinguish him from all the other Ralphs I was seeing?

So, date number seven came, and we had our romantic dinner, in candlelight, and talked about work. It was a dull evening – to be honest they had all been dull – but I was determined not to give up. There was the kissing to consider. There was the whole ‘having a boyfriend at last’ thing to consider, too. I’m not by nature a quitter. ‘Look,’ I said, ‘do you think … could we talk a bit more, between dates, so that we’re a bit more in touch with the day-to-day, what’s happening and what we’re thinking? I’d enjoy that.’

‘Sure,’ he said, scrutinising the wine list.

We had weird unsexy sex, and later on, back at home, having soaked in the bath, naked in fresh crisp sheets, I texted him saying that I was warm and naked in bed, just bathed, feeling restless and thinking of him. He didn’t reply. The following night, having turned out my light, I texted that I was thinking of him. That was all I said: ‘Thinking of you.’ The response was: ‘You take care!’ (Seriously. Really.)

It occurred to me that I frightened Ralph. Ralph was scared. It began to look, at the very least, like an unusually short attention span. Whatever the actual diagnosis, I knew it wasn’t going to last even a week longer. I needed romance, of some sort, some sense of a progression, some inkling of a relationship. I needed more than a fuck-buddy who didn’t want a friend. And that’s why I went quiet. I stopped texting and emailing, leaving a vacuum, to see what Ralph would fill it with. Ralph didn’t fill it with anything. It was easy come easy go, and it came and it went. Nothing was put to an end because essentially nothing had begun. He wasn’t in touch again, and that was that. It was as if the whole thing had been a hallucination.

I did start to wonder, at that early point, if a middle-aged woman on a dating site might be considered as really only useful as a fuck-buddy. I did wonder if men assumed I would know that, and that I’d take what I could get. I didn’t get a lot of messages unless I’d written first, and those I did receive tended to be only a notch beyond grunting. ‘How About It Darlin, You and Me? Xxxxxxxx’ There are plenty of men online who think a woman over 45 will react to the offer of a shag in an alley with tears of gratitude.

Men online use kisses, all the time; perhaps they picked up the habit on social media, where women who don’t know each other and will never meet have developed intricate hierarchies of kissing. This is a cultural shift. I’m sure men never used to scatter kisses so freely. Plus, a new function enabling people to send mass mail-outs had been introduced on one of the sites, which some men took to eagerly. It meant that they could write one message and press EMAIL ALL and have it sent to every woman they’d ticked. One such that I received acknowledged that it was a mass communication, as if that wouldn’t put us all off him, at all. ‘Hello ladies, this is Pete, I’m an average guy, like a laugh, like sofa and the telly, like my footie, like to make a lady happy, so let me know if any of you would like to take a chance on a 45 year old man: one careful owner, reasonable bodywork for age, full service history.’ Another had used the mail-out facility to get a lively competitive vibe going. He’d set us all an essay question. He wanted submissions in reply to the following: ‘Do what thou wilt shall be the whole of the law.’ It wasn’t clear what the prize was.

Other messages were misdelivered. An email arrived from a man in South Wales. ‘Jessica,’ it said, ‘I knew the minute I saw your face that it was meant to be. Do you believe in love at first sight? I’m visited by intuition that I am the man for you. Send me a long message telling me all about yourself, and I’ll reply by tonight, and we can get this thing started.’

‘You’ve sent this to the wrong person,’ I replied. ‘I’m not Jessica. I’m afraid this is the hazard of using cut-and-paste.’

‘You’re the right person,’ he insisted, styling it out. ‘I’m just not very good with names.’

After this I had daily on-screen dating site conversations with a man called Alexander. He was Dutch in origin, six foot four and the kind of blond that takes grey well, and looked good in his photograph, in dark jeans and jacket and a white shirt, with a big brown satchel hooked across his body, and a floral scarf. He was unmistakably not from around here. We met first on a Sunday. Well, we didn’t really meet. All we had to go on were photographs and the usual clues: carefully veiled descriptions of who we are and where we work; our likes and dislikes; our favourite films, books, music, food, places in the world; what we’re looking for and our ideas about the future. We didn’t reveal our real identities or email addresses. We didn’t speak on the phone, or see each other talking on Skype. It was a connection built – and then dismantled – entirely by typing.

After a few days, Alexander wrote a very long message in the middle of the night, listing all the women he’d ever loved and how they’d let him down. Dates were supplied and first names, and vivid descriptions. He was 55, and his second marriage had come to an end in the spring. It failed, he said, because the children were too much; he’d realised he couldn’t handle living with young children. He’d moved out and left his wife to handle them alone, other than for a weekend a month, when he took them to the zoo, like an uncle. He wrote that he was looking for someone who would make him feel more rewarded by life than his wife had. As time went on, that sentence bothered me more and more.

There are men who will take on the role of therapist and draw you out, who’ll draw it all out of you like knotted silk handkerchiefs from a magician’s pocket. This feels wonderful at the time. It’s only afterwards that you might look back and shudder. There are people who get a kick out of owning other people; some people own others by knowing their secrets. Some men want to engage in the dance, and some men only want you to dance, while they watch you. ‘Tell me all about your past relationships and what went wrong,’ he wrote, at the end of his own exhaustive list, and, feeling pent up, feeling the thrill of letting loose and being listened to, I did. Alexander, a man I had known for less than a week, disagreed with my analysis. ‘It’s obvious to me that your ex never loved you,’ he wrote. ‘I’m beginning to see that lots of people end up married to people they don’t love, though it can take them a long time to admit to it. Adultery is often the beginning of a search for something more real, and the sex is just a smokescreen. I realise that’s been my own pattern.’

When I tried to bring the conversation to an end, Alexander became even more assertive. He said he’d taken the red pill. Dating sites are awash with men talking about the blue pill and the red pill. It’s a frame of reference taken from The Matrix: if you’ve ‘taken the blue pill’ you’re someone who doesn’t want to face reality, happy to live in your illusions, while if you’ve ‘taken the red pill’ you see the world as it really is. (You think.) Among those who claim to have ‘taken the red pill’ are men who’ve gone through a bad divorce and know all about women, how we think and why, how men behave and why: it’s all become clear to them. I told Alexander that he didn’t really know me. He disagreed. He’d come across my situation a hundred times. It was the way of things, he said. I had my first serious case of dating site revulsion. Why had I said any of what I’d said to him, and told him my history, this arrogant stranger? Though I didn’t write that. I wrote that it had been nice talking to him, and that I wished him luck. His reply said: ‘I could say that I’d be back to talk to you at a later date, like all the other arseholes, but as you’ve already gathered, I won’t be contacting you again because it’s already clear you can’t give me what I need. This isn’t what I need at this stage of my life.’ Everywhere I looked there were people who’d hit middle age and were talking about stages in their lives.

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