The Gentleman's Guide

The gentleman's guide  |  Women  |  Style  |  Grooming  |  Decor  |  Culture


Dear oh dear oh dear. I've seen an awful lot of guys trying to flirt with girls. Walking up to a girl and saying 'You're fit' doesn't work, yet still they persist. Learn from your mistakes, and from the mistakes of others! Learn to flirt properly:

  • Who you should flirt with.
  • What not to do.
  • How to tease.
  • How you should view yourself when flirting.

The most important thing to remember about flirting is that it doesn't necessarily mean you intend to sleep with that person. It's a way to be close and friendly with a person you barely know, though it must be appropriate. Your boss? No. The 50-something secretary? Yes, if for no other reason than it's a good idea to have secretaries (and receptionists, security guards, cleaners and caretakers) on your side. Your girlfriend's Dad? You really need to ask? Your girlfriend's sister? Sure, after a few glasses of wine, so long as it's clear you have no intention of trying to seduce her. Personally, I see nothing wrong with flirting with co-workers, female friends, or even gay men, and I've done all of these. None of these people have really thought that I wanted to be intimate with them but it's fun and friendly. Best of all, it's great practice for when you do want to attract someone.

So, let's assume you've met an attractive lady who you'd like to get to know better. You start by complimenting her, because it's polite and women love compliments, right? Let's look at a case study, of someone I knew called Tom. He was infatuated with a girl I knew, and she was undeniably beautiful. He followed her around, did pretty much anything he could for her, and told her things like 'Your eyes are as blue as the Mediterranean.' I swear I'm not making this up.

He totally emasculated himself and got exactly nowhere. Sure, she was good friends with him, but he was essentially a shoulder to cry on; a reliable, steady, dependable person who she would never think of in a sexual way. You do not want to be this. As Gavin McInnes (Vice Magazine) notes, if you find yourself in this situation 'you're basically Ducky from Pretty in Pink.'

Confusing, eh? Within the seduction community (yes, there's a seduction community and no, you don't want to know) this is known as supplication. You're doing everything a woman wants without her ever needing to give you anything in return, and this is not flirting. Flirting is a two-way process and requires both people to make an effort. If you forget this key point you're not flirting, you're wasting your time.

So if being nice to a girl is a non-starter then you need to be a jackass, right? After all, although women may say they like men with intelligence and a good sense of humour, they often seem to go for arrogant gits. Well, sorry, but this isn't quite right either. What women really find attractive, more than anything else, is confidence. Unfortunately, arrogant guys have this in spades, so you need to beat them at their own game. Being a jackass isn't a stable foundation for a relationship; being confident, cool, and behaving like a gentleman is.

The key difference between you and the arrogant guys is that you are going to be nice to the women, though not until they earn it. I'm going to assume you've already read my guide to approaching women and you're OK at getting to the point where you're embarking on a conversation. So you're talking, and you need to give her a way to earn a compliment. Be cheeky. It's fun. If she hasn't really smiled yet then say something like 'Y'know, I bet you've got a really nice smile.' She'll smile. Trust me. Here's the clever bit; first you smile to show her that you like her smile and reward her, then you jokingly say something like 'Nah, actually I was wrong, maybe you shouldn't do that again.'

I know, confounding isn't it? If she looks annoyed then it wasn't clear that this was a joke - practise in front of the mirror if you really need to. If she can tell you're joking then she'll act disgruntled and maybe hit you in the arm, but she'll still be smiling. Yes, you just insulted her, but she's smiling. This is flirting. Essentially, you tease each other. For every two steps forward you take one step back. Maintain good eye contact (as I've said previously, if you have trouble with this then look at her mouth instead). You're not just giving her everything she wants, you're encouraging her to chase you to get compliments. If she does something really cool then say you think so. To balance this, go easy on complimenting her appearance (anyone could get that haircut, but not anyone can tell the funny anecdote she just did).

Your entire vibe throughout this experience should be fun, lightly sarcastic, and occasionally silly. Don't be planning in your head a sequence of a hundred things to say, just go with the flow and enjoy yourself. Flirting is fun, so don't make it into a chore. Don't give up everything you have too early; you should be ever so slightly out of reach. Initially, it shouldn't even seem like you're talking to her for any other reason than it seemed like it might be fun. If her friends are with her then flirt with them too, even if you're not interested. Flirt with them more than her and she'll feel compelled to work harder for your attention. Your side of the conversation should steer clear of any unpleasant subjects, and sport. Desperate Housewives, Big Brother and The OC are always good fallbacks if you're stalling. Keep the swearing heavily in check. Gentlemen shouldn't really swear at all if they can avoid it, but I'll concede that under rare circumstances it may be necessary. If you do, make sure you don't shout it and get at least one polysyllabic word close to it to remind your audience that you're an intelligent individual.

Don't be afraid to say things that aren't true. If she asks what job you do, then 'Rocket Scientist' is fine as long as you're not actually a rocket scientist. The aim is not to make her believe you're a rocket scientist; it's to be silly and funny. For goodness sake don't go researching what a rocket scientist really does, because it's far funnier if you're obviously trying to make it up on the spot. As seduction expert Mystery says, 'It's not lying; it's flirting.'

Mystery also has a great analogy for flirting. If you give a piece of string to a cat it ignores it, but if you dangle that string over it's head, just out of reach but close enough to try to grab, the cat goes crazy for it. You need to be that dancing string. You need to be the prize. You shouldn't be throwing yourself at her, you should be encouraging her to throw herself at you. Don't be afraid to tell her how to do this. If you've got a really good vibe going then saying 'OK, I've been talking to you for ages; I think it's about time you bought me a drink' can work wonders. At the very least, you're teasing her a little more and you can back down and go yourself to show you were just kidding around. If you can push it then get her to go to the bar for you. It demonstrate serious confidence, gets you a drink, and places value on your company.

In essence, what you're doing here is using the tricks women use when flirting. You're turning them back on the lady you want to attract. Men don't do this, and as a result any guys who do practice these skill effectively elevate themselves above the herd. This idea is at the core of being a gentleman, so make sure your flirting reflects what a great catch you are.

Get in touch: email me at [email protected]


Don't ever say you're desperate about anything. Desperate to get a CD or see a film or whatever? No! Skip other negative words too, and don't be afraid to work words like 'excited', 'thrilled' or other positive stuff in there. Thinking about this stuff will keep you clear of depressing conversational topics as well as subliminally getting her brain in a good mood.