GOTN Avatar

On how to chat up a woman

What do the following things have in common?

“Do you mind if I sit here?”

“I’m not really a ‘books’ sort of person.”

“Haha – your boyfriend’s a shortarse.”

Any guesses? Here’s the answer: they’re all things guys I’ve slept with have said to me shortly after I’ve met them.

How to chat up a woman

I’d be gobsmacked if anyone who writes about sex hasn’t been asked the question “So, how do I go about getting laid?” or something similar. I’ve been asked a fair few times, most recently I’ve been asked what someone should say to make girls like him. The generic ‘how to chat up a woman’ request. I’d love to be insightful and wise bout this, but unfortunately all I have is some very generic advice:

  • if you want to sleep with women, talk to them
  • listen to them, and try to establish whether you’ve got anything in common
  • make the most of the opportunities afforded by the internet
  • don’t be a dick

I think what the people who ask these questions are looking for is something more specific than this: some magic words or a few good conversation starters that will have the average lady slipping off her chair with arousal halfway through the first round of drinks.

I can’t do this, I’m afraid. And anyone who tells you they can is either incredibly deluded or having you on.

I’m rubbish at chatting people up. My technique runs from the obvious (send them a flattering message on OKCupid then hope that when we meet in person I am drunk/brave enough to suggest a shag) to the arduous (develop a friendship over the course of many years, cross fingers that one day they’ll fancy sleeping with the girl who’s been hanging around like a bad smell) to the direct (“Fancy a shag?”). The benefit of being appallingly bad at chatting people up is that I fully understand how difficult it is, and sympathise with anyone who has spent two hours staring at a stranger across a crowded bar trying to pluck up the courage to offer them a drink.

Redefining success

I don’t think anyone’s bad for asking – naturally anyone who’s had crap luck when approaching people they fancy would be keen to see if there’s a way to minimise any failures in future. So often I write about what people shouldn’t do, it might seem logical that there’d be something we should do to improve the odds. Unfortunately this is one of those issues where although there are standard things you should avoid when you’re trying to look attractive (being rude, for instance, or accidentally being sick on their shoes), there’s no guaranteed ‘hit’ technique.

As the original ‘lines’ in this blog demonstrate – you can say something either mundane or cringingly foot-in-mouth but still end up in bed with the person you approached. Likewise, you can wow someone with your charm and charisma and still end up going home for a lonely wank.

But (and I appreciate it might not seem like it when you’re lonely and keen to find someone) the fact that there are no magic words is a good thing.

If I were a charlatan, I’d tell you there are techniques that’ll have anyone eating out of the palm of your hand. But if that were true, the world would be an awkward and horrible place: one where we ended up getting together with people purely on the basis that we fancied them for five minutes. If you had a magic ability that meant anyone you liked would be persuaded to shag you, you’d end up shagging a hell of a lot of unsuitable people.

Can you think of anyone you fancied on first site but then ended up disliking? Because I sure as hell can. I fancy most liberal-sounding, scruffy-looking, slightly-nerdy guys I meet purely on the basis that I’ve had pretty decent luck with these guys in the past, and most of them have turned out to be both fun and hot. But that doesn’t mean they’ll all be. If I had Abracadabra’d all of them into bed, there’d have been plenty of awkward mornings in my life when both of us woke up and realised that we weren’t suited to each other at all.

So: chatting up. It’s never going to be 100% successful, and I can’t give you any advice that will make it so. Because your aim when introducing yourself to a stranger should never be as simple and boring as just ‘getting that stranger into bed’. Your aim, in my honest and unskilled opinion, should be finding out whether you both actually want to go to bed together.


  • Danny says:

    Oooh, I’m a liberal-sounding, scruffy-looking, slightly-nerdy guy on OKCupid and a long-time lurker here (although my profile is awfully Ned Flanders-esque just because guys on OKCupid that even remotely hint that they’re into a spot of kink won’t ever hear from anyone ever ever).

    If people ever asked me that the question of how to chat up a woman – which they wouldn’t – I wouldn’t have a clue what to tell them. Is there not just a general knack for being likeable, funny and with a glint of mischief in your eye? Surely that’s impossible for some. Ultimately, I suppose the advice is to be yourself and hope the other person matches your level of weirdness…

    • Girl on the net says:

      “guys on OKCupid that even remotely hint that they’re into a spot of kink won’t ever hear from anyone ever ever”

      Really?! I’ve found the opposite – OKC seemed to me to be one of the kinkiest sites. Usually I get matched (based on my question answers, presumably) with guys who have a tendency towards being dominant, and a desire to be a bit filthy in bed. Have you answered lots of the questions? The sex ones in particular can be your friend when matching you with people. Good luck!

      “the advice is to be yourself and hope the other person matches your level of weirdness…”

      Succinctly put, I agree =)

      • Danny says:

        I’ve answered about 500 questions so I think so. We’ve probably seen each other’s profiles at some point. I’ve included my username in the Email field of this message so feel free to indulge.

        I’ve been tempted to turn my nicey-nice profile into the kink-fest it really is (Dominance, gagging, tying, rough sex, babygirl/daddy relationship, etc) but I’m also half looking for a real relationship and just crossing my fingers they turn out to be a kinkster too. I’m probably not the only guy that thinks most girls read that and just think you’re a deviant, and not in a good way, a dangerous way.
        For the record, I’m currently in a dominant FWB relationship with someone I met on there right now.

        This entry reminds me of the entry you wrote about ‘The Game’, I’ve not read it but my understanding is that it’s half story/half instruction manual. Would you feel that a book of that nature for guys who are completely hopeless may be a positive thing?

  • These tips is working, i read these blog 3 days ago and i try your tips, yesterday i sleep my blonde co worker xD thanks for sharing really usefull blog.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.