One man goes on 40 online dates in a month | Men's Health Magazine Australia

I Went On 40 Online Dates In A Month. Here’s What I Learned

I don’t date. I used to, and I think at times I might even have enjoyed it. But after one romantic disaster too many, I reviewed my dating history and concluded there was something wrong either with a) every girl I’d ever dated or b) me. Now I’m ready to give it another shot, because […]

I don’t date. I used to, and I think at times I might even have enjoyed it. But after one romantic disaster too many, I reviewed my dating history and concluded there was something wrong either with a) every girl I’d ever dated or b) me.

Now I’m ready to give it another shot, because I’ve hit upon a theory – one that will exorcise my dating demons and turn me into a great seducer of women. It’s called meta-learning and, while it sounds like Game-style pick-up artistry, it’s far less arch. The theory goes that when you’re learning a skill – whether it’s ninjutsu or 21st century mating rituals – you’ll make greater progress if you practise intensively.

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For the next month, I’m going to date as many women as possible. If it works, I’ll be cruising through meet-ups on a kind of irresistible autopilot. But there’s a lot of catching up to do, as I discover when I sign up for a dozen sites, apps and singles nights. There’s been a revolution in sexual practices that passed me by (have you seen Tinder?). I’m a dinosaur – a missionary man in a reverse-cowgirl world. Which is all the more reason to get started.

Date #1 An inauspicious start

Coffee on a wet Friday with V. A couple of hours beforehand I have a pep talk with dating expert Hayley Quinn, who warns me that coffee dates often seem like job interviews. She’s right. V is a floor manager for a major department store. I buy her a latte and we talk retail. I might as well have met her on LinkedIn.

Later, I line up dates on the various websites I’ve signed up for. I’m horrified by how much time it takes. While marvelling at OkCupid (seemingly designed for egomaniacs and oversharers) I decide a bland profile is best. After 30 minutes on Tinder – the app that lets people hook up with the swipe of a finger – frantically registering my interest with no regard for acne, bodyweight or bad teeth, I’m rewarded with several matches.

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Date #2 The laws of attraction

I’m met by E on a freezing Sunday night. I take her to a bar. She’s originally from Riga, and works in for an oil company. Tall, curvy and classy. I feel too weekend-casual in jeans and a cardigan. Brogues will be a rule from now on.

Quinn’s advice is to ignore the dating cliché that asking lots of questions will win women over: “Volunteer information about yourself – it encourages people to open up.” I talk about my upbringing and, blow me, it works. E re-applies her lipstick in the bathroom. A good sign, I’m told. If we’d met on a Friday, who knows what would have happened. But work is looming. A lesson: don’t meet attractive women on Sundays.

Date #3 Lost in translation

R is Japanese – lovely, totally incomprehensible. I think she enjoyed our chat but it was hard to tell.

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Date #4 My first Tinder match

I eat lunch with J from Croatia. When she was a baby she was kissed by Marshal Tito. I produce a biography of Tito from my bag but the coincidence fails to stimulate conversation. We don’t linger for dessert.

Date #5 Second swipe

M is also from Tinder. She’s Italian, sort of like a sexless Sophia Loren. I’m becoming dispirited.

Date #6 Three’s no charm

My third date of the day is L. She recently suffered a nervous breakdown. Never mentioned that in her profile.

Hunting for women is already preventing me from doing more enjoyable things; I have Chapman Pincher on my Kindle. It was a mistake to stack multiple dates in a day. It removes any thrill – a concern considering I have eight dates scheduled for the next two days.

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Date #7 A blast from my past

I meet a former colleague, C, who I’ve been lusting after for years. I buy her a pie. It’s a pretty good pie, too, but she doesn’t go over.

Date #8 Friendly fire

S from Tinder is smiley and chatty with faultless social skills. I don’t trust it.

Date #9 Judging on face value

Wine with M – the first date I’ve really enjoyed, and the first woman I found attractive just by looking at her photo. The algorithms that sites use to match people seem somewhat redundant post-Tinder, where appearance is everything.

Date #10 Devil in the details

I end the evening at a singles night. After a couple of false starts, I unwittingly use a blinding opener to attract C: “Nice bracelet.” This half-arsed hello is, remarkably, golden. Apparently women like someone noticing little details in their outfit. Noted.

Conversation – or the lack of it – has been playing on my mind. I call Sean Brickell, a public speaking coach, and relay the day’s chat to him in the hope of reassurance. I didn’t do well. “Silences at the start of conversations are image killers,” he tells me. “If you want to appear confident, be armed with something to open with. Inane is fine. Talk about the weather if you have to.”


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Date #11 Sweet retreat

K from Tinder is a nice, slightly chubby nanny. I suspect she would put out if we met over wine, rather than coffee and cake.

Date #12 Playing out of my league

My four o’clock, J, is an attractive career woman in her forties. She’s a better match for Maurice Saatchi. My weather chat flounders.

Date #13 Location, location

Sublime planning means I only have to walk 100m to my next date, B, who sadly hasn’t walked 100m herself in quite some time. We enjoy a glass of wine.

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Date #14 Stacking strategies

My second nanny of the day, teetotal L. Delightfully dim but, that apart, she’s not my type.

Arranging dates in a small geographical area is vital if you’re stacking, but timing is a minefield. A coffee date never runs late; dinner might. I dribble out the same chat and by the fourth date, I just want to go home. Not a single one of my marathon dates contacts me for a second meet-up. Inane openers do break the ice, but stop you from reaching anything deeper. My approach needs an upgrade: I’m going to add a little controversy going forward.

Date #15 Running on empty

It’s a Friday and I’m emotionally exhausted. Thankfully my date with G is over quickly. I crave male company so go home and watch Expendables II.

Date #16 A better press

A Saturday afternoon cuppa with C. I discover that coffee dates can work when you’re not in the office headspace. I practise my controversial conversation. I tell her I was running late and had to elbow a granny out of the way to get off the train. She laughs and soon we’re both giggling away. A good date.

Dates #17-21 The numbers game

I head to a nightclub for speed dating, counting each four-minute contact as 0.25 of a date. The scatter-gun concept works: by the time I meet my fourth woman, the jitters that can ruin a more conventional date are gone. I leave feeling confident, but have to wait for feedback next week to find out if my self-belief is justified.

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Date #22 Taxing conversation

I spend Sunday evening with F, a petite Spanish peasant. She’s furious about the amount of tax she pays; I pick up the bill for her three large Merlots and head home alone.

Date #23 Raising my profile

A Tinder girl cancels, as I’ve failed to “banter” on WhatsApp. I re-write my profiles and spell out that I want a girl with lovely hair and boobs as I have neither and would appreciate the novelty. I also add four Red Flag Words: “banter”, “hygiene”, “spiritual” and “Canadian”.

Date #24 Fishing for a complement

J is a six-footer. She works for BA. Her legs are dramatic. It’s a Monday and her week-long shift begins early, but we still manage three drinks. I like her. I tell her about my writing, my website, my passion for the Balkans. I’m doing what I was advised – banging on about myself. And it works.

Afterwards, I’m brought back to earth when I find that only three of the women I met at speed-dating have expressed any interest in me: a hit rate of 15%. Jesus.

I book another spot next Saturday to see if I can do better, armed with new tips from my dating coach: I am told to be self-deprecating in my humour; stories that show me as a protective person are encouraged; my eye wandering must be on point, too – from eyes to mouth to neck with the odd chest glance. Top of the chest mind, not boob ogling. Research says this works. Which works for me.

Date #25 High-risk tactics

Another Spaniard, A. I treat her to a moderately priced pizza and the house red but, after a science-backed cleavage glance, decide to up the ante. Advice from Quinn: “If you think you’re getting on well, say something risqué. This appeals to a woman’s sense of danger – she’ll run with it if she likes you.” I try it and we’re soon talking about sex. She wants to meet again.

Still on a high when I get home, I feel a change in myself. I rejig my profiles to make them punchier. All of the women I’ve clicked with have enjoyed off-colour comments. Perhaps the more ‘Vegemite’ my profile, the better? When playing the numbers game, a controversial personality will strike gold at least some of the time, where something blander could easily pass straight under the radar. My latest lesson: don’t be afraid to offend.

I meet up with Quinn, who wants to teach me that it’s OK to approach women you don’t know without the safety net of a computer screen. Pick out something noteworthy about them (shoes or haircut, presumably, not her huge nose). I’m eaten up with nerves but have no escape. I tell three girls I find them attractive and would like to take them out for a drink. One is engaged but the others give fake numbers. Incredible.

Date #26 La Dolce Vita

The next night, I go to another singles event. A spectacular standard of women. I get chatting to an Italian and, just as I’m leaving, she offers me her number. It’s a beginners’ sales technique: always be leaving. Appearing like you’ve got somewhere better to be is pure magnetism. And another observation: these are cool bars. The fact that I was there at all put me in a good light. A ‘halo effect’ in marketing terms.

Date #27 Illicit encounter

Back on Tinder, I meet M: pretty, with a frankly pornographic body. I open with a general comment on the rain but add that I stole my umbrella from a market stall. The fact that this excites her terrifies me, but we agree to meet again.

Dates #28-36 Less haste, more speed

I approach my second speed dating night with trepidation. Last time I was a little too enthusiastic, too try-hard. I’m wearing exactly the same clothes for control purposes. My dating uniform: Reiss blazer, Emmett shirt, Levi’s, Barker brogues. I take charge of each conversation but try to appear aloof, leaning back in my seat; these girls are actually working for my attention. I make a point of examining each. As seedy as it feels, I want them to know they’re in the shop window as much as I am. I’ll find out whether this all works in a few days.

Date #37 Failing chemistry

Afternoon coffee with D. Decent chat but no sexual frisson. In the evening, I have dinner with T – the Italian women I met at the Inner Circle singles event. She looks great, but she doesn’t drink, is gluten intolerant and won’t eat anything containing onion. It’s a no from me; I’m fussy. Suddenly my phone is buzzing with messages – the busty Pole, the 6ft Scot. I book them both for second dates. I can’t think of a single thing they have in common. Why did we click? The only common factor is that I bossed the conversation on both occasions. I’m combining what I know is working: funny opening gambits; aloof body language; appearing busy; nice brogues.

Date #38 Voicing an opinion

I hit a new dating night called 4 Ladies 4 Gentlemen, and postpone the Scot. I spend the evening flirting with a voice coach. Although she’s attractive I can’t imagine having sex with someone who enunciates so clearly. Polish M blows me out at the last minute; she has a presentation to prepare, can we do Thursday instead? The Scot has stopped responding to me. Postponing the previous date must have upset her. Dating is an insecure business.

Date #39 Behind at the bar

Tonight, an 8.5/10 pub date with A. She’s pleasant, attractive and appears to enjoy my joke about stealing a child’s bike to dodge the traffic. I upgrade her G&T from Gordon’s to Hendrick’s, but it proves to be a futile investment. I get an angry message from the Scot. She’d suffered an anaphylactic shock. This is brilliant news – it means she hasn’t been in a huff after I postponed our date. She’s in a huff now, though, furious at me for assuming that she had ignored me.

Date #40 Exit the game

Heading home, I arrange to meet an ex. The ex. The emotionally devastating ex. The next day, we grab lunch but judging by her body language, this is the lowlight of her year. Possibly even her decade.

Unwilling to end on a sour note, I meet the Pole. I’m still in a strange emotional state following the ex encounter. We drink too much wine, then go to a god-awful club. I remember dancing, a horrendously expensive cab and a dingy flat in south-west London. I’ll draw a veil over what happens next but I’m there till 4.30am, at which point I make my excuses and leave.

In the cab home I try to figure out what went right. It seems straightforward. I found her attractive. Presumably she likewise. We drank a lot. We talked. We drank a lot. My miserable encounter with my ex left me distracted and naturally aloof. There had been some ‘banter’ in the run up to the date. But really we just clicked. That’s it. Without noticing, confidence came naturally.

Before dragging myself to bed I drunkenly check out my hit rate at the second speed-dating night – six women would be happy to hear from me. The stats don’t lie: I’m now twice as good at dating as I was a week ago. I don’t email a single one. It’s time to call a halt.

Did I enjoy the experiment? No. Would I recommend it? Yes, absolutely. A period of intensive dating is hugely beneficial if you ever clam up around women. If you’re meeting three girls in a day, your emotional investment in each date is dramatically lower than it would be if you were seeing, say, one girl a week. It’s an automatic confidence booster, which is welcome on a dating scene where women are becoming increasingly savvy and demanding consumers.

I can’t see myself using old-fashioned dating sites again. Tinder renders them pointless. Moralisers miss the point. It’s not another step on the road to Hades, but a return to the traditional way of meeting girls where, if you saw a woman you liked, you’d approach her and offer to buy her a drink. And that’s the biggest lesson here. For all the digital sophistication – the complex algorithms, salesmanship and extreme disclosure – coupling still works best when you can boil it down to: “I like you” and “I like you, too”.

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