How To Talk Someone Into Sleeping With You: The Art Of Conversation

Dear DD,

On a first date, how do I talk a girl into liking me, being my girlfriend or having sex with me?


Confused Men of Australia Inc


Dear Confused Men,

I’m so glad you asked! You’re already on your way. Here are some steps:

  1. Stop talking
  2. Ask a question
  3. Listen
  4. Repeat

Best of luck,



Dear DD,

Thanks, but what should we ask?


Somewhat Less Confused Men of Australia, Inc


Dear Somewhat Less Confused Men,

You’re getting the hang of it now! Here are some entry level questions:

  1. Ask me exactly the same question I just asked you.
  2. Ask me to tell you more about something you already know about me.

Here are some more advanced options:

  1. Duck to the bathroom and skim through my online dating profile, pictures, online banter – these are all good convo starters
  2. Go backwards. Ask about my childhood, studies, adventures, favourite memories.
  3. Go forwards. Ask me who I want to be, what I want to do.
  4. Go hypothetical. Ask what I’d do if I won a million bucks, if I were in a zombie apocalypse, if I only a week to live, could curate any music festival lineup, could have any six people to dinner, be anyone else for a day, have the perfect day or have any super hero power.
  5. Go deep. Ask me what I really give a shit about.
  6. Go well. Be polite. Be different. Be confident. Be open. Be kind.
  7. Go now. If we’ve been yarning for an hour, call it a night before you run out of things to ask. Leave on a high rather than waiting for a low.

I genuinely want to know who you are, but I want you to know me too. We can’t get to know each other if one of us monologues or feels like an investigative journalist interrogating all night. It should be like tennis. I ask you a question, then you’ve got the ball. You have it for a while then hit it back to me- both of us take responsibility for keeping the ball in the air. On a first date it’s pretty rare that we’ll be relaxed enough for witty repartee, but we can try to draw out something from each other that interests us enough to want to see each other again to find out more.

I am thrilled that you have the collective self awareness to incorporate and ask questions! I sincerely wish you all the best and I look forward to far fewer boring dates from now on!

With increasingly fonder regards,




PS: For tips on squashing small talk see here and here. 


8 thoughts on “How To Talk Someone Into Sleeping With You: The Art Of Conversation

  1. I want to laminate this blog post and hand it out a public service to the men of this world.

    Nothing more frustrating than meeting a good-looking guy and quickly realizing that all the balls you are hitting so eloquently off your racquet are disappearing without a trace into the opposite court. Not even an attempt to hit back my serve; yet you still expect to “hit that”? Yeah, no.

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