My wife moved out, and within a fortnight had moved in with one of my best friends. When the news broke I was standing outside a newsagents at Clapham Common just after the pubs had shut, and I slammed my fist into the unyielding metal shutters, setting off a burglar alarm. I ran home, and for what seemed like weeks I took my anger out on soft furnishings, weeping uncontrollably, and intoning the word “why?” loud enough to register with the neighbours and inquisitive passers by. But during this period there were no offers of emotional support, still less nourishing casseroles or impromptu bursts of care and affection. So I went out.

And when I was out, I met friends, I met friends of friends, I talked about it until I’d used up all the cliched metaphors for my situation and had started moving on to gardening and show-jumping ones, none of which really helped me to make any sense of anything. But people listened, and all agreed I was displaying hitherto unknown levels of maturity and optimism. I was told that my openness and candour were fantastic assets, and someone else mentioned that maybe this was the best thing that could have happened to me. But as I trudged through industrial estates in the small hours kicking litter and howling drunkenly, this seemed irrelevant and very possibly wildly inaccurate.

Some people were so taken with my ability to weep openly in public that they formed emotional bonds with me, bombarded me with text messages, emails and phone calls. These people were invariably attached women and it didn’t help me one bit. I was a confused boy, and I remained confused for a long time. After nine months or so I was meeting no-one new and single, and in that supremely shallow fashion so looked down on by those with sensitive and caring partners, I was desperate for a sensitive and caring partner. I wasn’t ashamed, however. Being on my own was rubbish, and I was prepared to take slightly desperate measures to resolve the problem.

My advert said something like: “Cynical but benevolent 30 yr old seeks unconvential creative girl for gigs, galleries, giggling, and who knows, maybe less?” I thought this indicated an appropriate level of disbelief that such a thing would actually work, but immediately I started receiving voicemail messages, albeit a bizarre collection. Some people would mumble in an embarrassed fashion and leave completely inaudible contact details. Others would ring up with a streaming cold, making spluttering and mucus laden apologies which just left me thinking, why couldn’t you have taken some Lemsip and waited a couple of days? But I did end up meeting two women.

The first was someone 6 years older than me who walked dogs for a living. It was probably not destined to be a match made in, well, anywhere. As I turned up she looked at me as if I had shit smeared on my forehead. Towards the end of her orange juice she emphasised how she enjoyed doing this kind of thing to “meet a wide range of people”, while simultaneously backing out of the door. It was disastrous. Fortunately there was still one more to look forward to.

She was a conceptual artist of some note. She’d just lost her day-job and was actually in the depths of despair, but my emails lifted her immeasurably and she looked forward to them, replying quickly, and wittily. I sent her my photo, she sent me hers. She was boyish and very beautiful, I was boyish and much less beautiful, but nevertheless we decided to meet up. For reasons I will never understand, I decided that we should rendezvous at a multimedia tribute to Kurt Schwitters at the Victoria & Albert museum. As we went in, I immediately clocked about eight people who I knew, which was annoying as until then I’d managed to keep the whole personal ad thing a private and clandestine operation. The second thing I noticed was the deafening row. About 16 performers were evenly spaced on podia around the foyer, improvising with little regard for each other and creating a hideous melee of sound. Even to seasoned appreciators of art it was a disorientating and unpleasant experience. After 15 minutes she turned to me and said that she could handle neither the man hitting a trombone with a mallet, nor the stigma of meeting somebody through an advert, and she was leaving. Weeks of anticipation of going out with this talented and undeniably funny person were shot to pieces in less than an hour. She walked out and I hid behind a statuette to mope in a damp fashion and try and get some perspective on it. I couldn’t. Bizarrely, it felt as real as any rejection I’d ever had. I dove for the safety of South London and a friend’s Burns Night, where I slung back copious quantities of single malt and didn’t bother soaking it up with neaps or, indeed, tatties.

Lesser men may have taken these knockbacks as an indication that the dating game can’t be contrived, and that the seasoned procedure of encountering someone who is drunk at a party, while you are also drunk, at the same party, is a far more reliable method. But no-one I knew was having a party, so the horror continued, this time via the murky medium of the internet.

Online dating is big business. There are dozens of sites, all of them fearsomely populated with potential beaus, all of whom have paid up between 15 and 30 quid to have their “profile” listed. I enthusiastically joined the throng, and quickly realised a couple of things. Firstly, a large number of people really really enjoy “going out with their friends.” They love it. And what’s more they feel the need to remind you of it. This is so redundant and undescriptive they may as well have said “I enjoy breathing, and also producing insulin.” Secondly, women with pseudonyms such as “SmoovB” will try and entice you with straplines like “sweet lady wanna be yours”. I can only imagine that this person didn’t actually want to be mine, or else she wouldn’t have said that.

Thirdly, people lie. Or at the very least they lie by omission. Emma was first person I met through the internet, and her correspondence was lucid, funny, and very charming. We arranged to meet in a pub in South Kensington, and I told her she’d know who I was as I was carrying a battered and distinctive red bag. I went in, bought a drink, and as I turned around I saw someone waving to me, and she was possibly the largest woman I’ve ever seen, certainly the largest woman I’ve ever talked to. Now, I’m no body fascist, being no gazelle myself, but as the conversation continued she revealed that she had broken just about every bone in her legs and feet due to a hazardous habit of falling down flights of stairs. Realising that there is a stage at which people can no longer look after themselves properly, and that I didn’t really want to adopt the role of carer, I decided to be utterly straight with everyone I emailed. Even passive deception was going to be pointless.

The dating experience continued to be fairly grim. Sarah met me at Balham tube station, and as we walked up the hill it was clear that she was going to say very little, still less start a conversation. By the time we reached a pub I was sweating with the sheer effort, and had exhausted pretty much everything I knew about her – I even remember with a shudder saying something vapid like “So, you’re from Widnes, what’s it like?”. Mindful of the experience with the conceptual artist, I asked her if she wanted to go home right then, but was astonished to hear that she was “having a nice time”. God. You cannot imagine the struggle I had to keep idle chat for the duration of one solitary drink. I almost burst into tears at the strain of it all. Sarah and I did not embark on a fruitful liason.

Who else? Uh. Eleanor was bolshy, enjoyed gambling, drinking and shouting. I thought that meeting this kind of girl might yield different results, as I’d normally be seeking someone who might have just got back from the craft shop, casually tying her hair up before opening a bottle of Merlot to keep her spirits up and embarking on creating some far-out pottery. It was certainly different. We met, got battered on gin and tonic, and as I was about to say my goodbyes I heard the words “so, you’re coming back to my flat?”, as she set off up the road. I pursued nonchalantly, and when she asked “OK, are we going to sit up and chat, or go to bed?”, I’m sure I heard myself say “Er, bed please.” And as she undressed she announced, matter of factly, “ok, we’re not fucking, because there’s no condoms, but you can come in my mouth if you like.” I’m sure that many men would see this as a result, but I was honestly terrified. I was experiencing one dating extreme after another, and all I wanted was some safe middle ground.

I’ve missed out so much. The American who emailed me repeatedly from her hi-rise block in Chicago, indignant that I wasn’t willing to strike up a casual transatlantic affair. The city girl who pursued me avidly, called me every evening for a week, sent me text messages in French, but then on meeting up saw my copy of The Guardian and exclaimed “oh my GOD you don’t read THAT do you”, and subsequently became utterly frosty. The TV producer who didn’t look at me once for 90 minutes and just stared out of the window of the Covent Garden cafe whilst talking (I think she was talking to me.) The 22 year old singer who, in the middle of a noodle bar, said “look at my pants, they’re disgusting”, seconds before showing me her admittedly disgusting pants. The office temp who stared at me with big, sad eyes and confessed to being bullied at school, and was now being bullied at work. And most galling of all, the feature writer who wrote about our date in a Sunday supplement under the heading “Diary of an Internet Dater.” There’s nothing quite like learning about the state of your relationship with someone through the medium of the national press.

The game was ruthless, cut-throat and terrifying. I was usually judged instantly and wrongly as being sullen, uncommunicative and slightly distracted, and contrary to all my feelings about relationships I found myself judging other people instantly too. I can think of no worse way to get to know someone than to sit across a table from them for 3 hours, with no other distractions, and compete vigourously at being interesting. At best it was like a slightly strained chat show, with libraries of old anecdotes trotted out one by one, at worst it resembled the most stressful of job interviews, with added wild cards of lager and vodka.

The final straw came one Sunday, when I saw a profile of someone who shared my left-field musical tastes and who obviously didn’t take herself too seriously. I emailed her at 4.30pm. She emailed back at 5.15pm with her phone number. I called her at 5.30pm. We arranged to meet at 6.45pm. By 7.15pm I felt utterly uncomfortable and could sense that this was probably reciprocated. I was back home by 8.30pm. I had had the thrill, the excitement, the disappointment and the sadness that you might get over a 4 year relationship, but this was in 4 hours. I firmly resolved that this would be the last nightmarish emotional rollercoaster I’d be climbing on, without realising that the billing policy of the website in question consisted of debiting your credit card automatically every three months unless you specifically requested otherwise. So my internet dating persona was merely dormant, and in fact awoken last week when an unsolicited email arrived out of the blue from a cycling-mad architect. So we’re meeting at the weekend, but this time, regardless of how great she might seem on a computer screen, my expectations are going to be less than zero. “Even more cynical 30 year old still seeks…”