Street Life! - Picking up

Dear Sydney, there's nothing I won't do for you. I've taken much from your bounty over the years – your weather, your energy, your lifestyle, your blessedly long distance from my previous home of Adelaide – and I think it's about time that I gave something back. Specifically, Sydney, I wish to be your Andrew P Everyman: a roguish, sideburned crash test dummy for you to load into the car of hypothesis, set running down the straight of experiment and collide explosively into the solid wall of discovery. And for the first of what will hopefully become a series of amusing humiliations, I accepted our editor's challenge to go out on the pull, as it were, with master pick-up artist Neil Strauss, author of The Game.

Now, I'm not a shy fellow by any stretch – dignity and I parted ways long ago - but there's something about wandering up to some unsuspecting miss and dropping lines upon them that seemed... well, sleazy. But the way Strauss tells it, a sleazy pickup means you're doing it wrong. A true pick-up artist is charming, funny, quick, confident and engaging: one is only a sleaze if one's attentions are unwelcome, and the pick up artist is never unwelcome, if he does it right.

According to Strauss, looks are only moderately important in the pick-up game: which is advantageous, since my own physical appearance has been variously described as "not all that bad, I guess", "those shoes are quite nice" and "not deformed, at least according to strict medical criteria". And Strauss himself is no oil painting: he's an odd-looking dude, although possessed of an undeniable charisma. Yet if even half the things he's claimed are true, the man's enjoyed more sweet action than most medium-sized cities. 

After sizing me up, Strauss had the following advice:

1. Nattier threads. While appearance wasn't the be-all and end-all, the Andrew P Street look – which fashionistas the world over have raved about in terms ranging from "aging indie hipster" to "fallen backwards into a Brotherhood bin" – could use a moderate upgrade. "Think Kings of Leon offstage," he advised.

2. Don't lean in – speak up. My beautifully modulated baritone might rumble like the world's sexiest freight train, but it doesn't necessarily carry well in a front bar environment. For those situations I adopt a charming alternative voice, or "drunken bark", which can be heard through lead and can shatter crystal. Strauss, however, suggested that I should favour voice A, but speak up. Leaning is a no-no, since it's physically imposing, not to say downright creepy.

3. No apologies to open the conversation. No "Sorry about this..." or "Pardon me, but..." conversation starters. Strauss advises that would-be up-pickers should be confident and forthright from the get-go. He made no suggestions as to what would constitute a good introduction though, so I created a preliminary list of my own – for what woman could resist being intrigued by a man who announced his arrival with a spirited "By thunder!", "Ahoy!" or "Gadzooks!"?

Of course, as the old adage goes, the proof of the pudding's in whether the pudding can chat up women in bars – and so, from our perch in the Establishment, I was tasked with the challenge of walking up to a well-dressed blonde woman whose attractiveness was wildly, overwhelmingly out of my league. And as the entire table leaned in conspiratorially, Strauss laid out my instructions:

1. Approach
2. Start conversation
3. Continue it for as long as I could

It would have been easy for her to see that I was with a bunch of people, but he explained that was actually a plus: I was with friends, so therefore not an antisocial freak - immediate value-add. Also, it meant that any conversation I started would have an end as I'd presumably rejoin my friends at some stage. As far as she was concerned I was en route to the bar, just casually walking by, having had a fascinating conversation with my peers. The perfect crime.

Making the last minute decision not to bellow "Gadzooks!" I strode over to her and, in a clearly audible but still undeniably manly fashion, cast off with the conversation starter with which Strauss had equipped me seconds before.

"Say," I began, gesturing vaguely back from whence I had come, "we were just talking over there about relationships: what do you think the difference is between 'loving' someone and being ‘in love' with them?"

Initially surprised, she thought about it for a moment before smiling broadly and answering the question. I didn't even listen to what she was saying, concentrating entirely on smiling and nodding and looking interested. When she stopped, looking up at me with a hopeful smile, and I immediately complimented her – suggesting that her insight was worthy of a chat show with her name in the title. And so the conversation continued until I excused myself to grab a glass of water and navigate back to the group for my assessment. Strauss gave me a B and suggested that I not use my hands quite so much.

On subsequent attempts, I learned the following:

*The conversation opener should be fun and easy to contribute to. Suggesting a good name for a friend's new puppy scored me some lovely chats; asking her thoughts on the likely results of the Stereo mission to measure solar coronial activity was less fruitful. That being said, if anyone had offered an answer involving potential planetoids gravitationally locked in Earth orbital path, I'd probably have proposed on the spot.

*Keep the conversational plates spinning. While you're keeping her engaged, she has no opportunity to think "Hold on, who is this person and why the hell am I talking to him?"; and besides, if you're being conversational and entertaining then she's less likely to want you to leave.

*Have somewhere to go. No one wants to feel as though they've been leeched on to by something they can't remove, but also that moment when you say that you should freshen your drink/rejoin your friends/finish off that vampire you were midway through vanquishing is the moment when you find out just how damn charming you actually are. Are they suggesting you come back, merge groups or talk later, or are they smiling and wishing you a good night?

*Don't hit the piss. Strauss is very clear about this: a pickup artist doesn't drink on the job, using his clear head and nimble wit to weave his web rather than relying on the false bravado of half a dozen gins and tonic. However, purely in the interests of comparison, I thought I'd see how different the experience was made by alcoholic intervention, and my results were as mixed as my drinks. One thing was clear, though: tequila definitely blurs the subtle distinctions between "elegant seduction" and "drunken harangue".

The question of course remains: did I pull?

Well, a gentleman never discusses those sort of things. Besides, this was written on a tight deadline - I could hardly waste value data-gathering time on petty lovemaking, after all. But I do have a few new numbers that I'll be calling as soon as the magazine goes to press... if only to make my move before they read this.

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