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. 


Valentine’s Day: A Solo Survival Guide

Dear DD,

I hate Valentine’s Day. I just want to be able to leave the house without my own singledom slapping me in the face six billion times as the whole world celebrates what I don’t have.

How can I make it through the day without crying on the couch watching ‘She’s All That,’ or going on a jealous rampage, flipping candlelit tables and stuffing red roses into the drooling, lovesick faces of happy couples?


Grumpy and Lonely in Karratha


Dear Grumpy and Lonely of Karratha,

First up, I am truly sorry that you happen to live in K-Hole. I’m quite sure it’s the only reason you are single. Secondly, Grumps mate, I feel ya! I’ve been there buddy. You might be very Happily Single for 50 weeks of the year but the fortnight leading up to V-Day you become Pretty Uncharacteristically Desperate. That entire aisle of red love heart themed merchandise at Woolies, the ‘for someone special’ tagline added to every ad on telly, the overheard plans of people in couples, the romance novels on decorative display at the local library – all this noise can test even the toughest of lonely hearts.

Despite the fact that Karratha is now a city and not a shire (controversial!) there’s still no cinema for you to see ’50 Shades of Grey’ at, there’s no cool anti-capitalist hipster bands playing anywhere and you probably don’t have any single mates to hang out with either. They’re probably on the east coast being each other’s Valentines, going dancing and having a great time.

Soz to add to your (probably constant state of) FOMO but it looks like you’re gunna have to get yourself through this one. Don’t let small town syndrome strike you down!

Just avoid the Centro Mall. Avoid restaurants. Don’t attempt to circumnavigate the CBD solo and unassisted. It’s not the day for self-dates reading a book in a cosy café corner, that’s if the café has any tables for one. You’ll cringe at so many cute couples you’ll end up a cranky cynic hell bent on preaching anti-consumerism to waiters who aren’t flirting with you, they’re just giving you good customer service.

In fact, don’t just avoid the ‘CBD’ avoid Karratha. The only way you can truly escape is to get outta town. Here are some simple steps:

Step 1: Ask some old people where to go and head bush for the day. Tell someone where you’re going and pack plenty of water, fuel, swimmers, good shoes, hat, suncream and the unhealthiest snacks you can find.

Step 2: Crank your favourite tunes and podcasts in the car. Call up those east coast single friends with your hands free headphone set thing. Stop whenever you damn well feel like it. Take some photos. Pick those flowers. Get as many Cornettos and boxes of Pizza Shapes from shitty roadhouses that you want.

Step 3: Drive for at least an hour. See that country changing. Pull over and stand on top of your car to get a good view. Walk over to that tree over there. Sit on that nice rock in the shade then close your eyes and do some breathing in and out for a bit.


tree sunset karijini pilbara

Take off your shoes and feel the sand. Call out to the country if you want. Step into that waterhole slowly. Keep going. Slow though, so you can feel it tingling up your body. Let that freezing cold water cover you all the way up to your shoulders. Stand there shivering for a while. Look up at those cliffs and how those trees just seem to grow out of the rock.

See those little clouds in that big blue sky above you.

Listen to those birds and that silence.

Take a deep breath in.

Close your eyes.

Duck dive down.

Go on! Put your head under the water, I dare ya! I can 100% guarantee it will feel amazing.

Lie on your back for a while, faff around in the water for a while, then repeat Step 2 in the reverse direction and sleep happy in the knowledge that tomorrow your photos will win the internet and chocolate prices will be slashed.

You’ll be right, Grumps, you right.

Best wishes,