Drawing Dates - Drawing for Delight

When is the last time you let yourself play?

Dear hard-working, stressed out, “I can’t ever get it all done no matter how much I try” responsible adult.

I understand how important it is to focus on getting stuff done, how little time there seems to be, and how desperate you are for a break.

I am an overachieving perfectionist with an anxiety condition who has worked herself into the ground several times and suffered spectacular health crashes as a result.

I’m here to let you know that it doesn’t need to be this way. Carving out time for creative play for the sake of it, with no pressure to make it “good” or be anything in particular, can completely transform your life. I am the proof! I want to share my process with you so you can find some relief, too.

Rose Wintergreen artist drawing with strangers_photo by Shallinda Coreen.jpg

Is this you?

  • You never seem to have enough time for play.

  • You would like to do something creative but you have a voice telling you in your head that you are not allowed to make anything unless it’s going to be “good” or help you with achieving some sort of goal or project outcome that will earn you income.

  • You have a voice in your head telling you that drawing is something only a chosen few are allowed to do, people who were born with innate talent, other people, not you.

  • You remember the joy and freedom of drawing just for fun back when you were a really little kid, and it makes you sad that you don’t create with that same lightness anymore.


You need:

  • An appointment with a set time to help you prioritise time for play.

  • A relaxed, fun environment where you can just be and enjoy exploring, with no pressure to make anything in particular. An opportunity to meet yourself in the moment, exactly how you are, no need to push or strive.

  • Time with a prolific, professional artist who really gets what it’s like to live with a strong inner voice saying “I’m never going to be good enough, so there’s no point in starting”, but has found loving, joyful ways to defy it and to enjoy the creative process even when it doesn’t go as expected.

Happy customer - Yani.jpg

It was nice to unwind and create.

I don't know of anyone else offering this. It's a worthwhile experience and a fantastic opportunity to share time with an accomplished artist. - Yani, 31, warehouse supervisor


Cut yourself free from your inner critic and let yourself play

Come on a one hour drawing date with me, all materials provided!

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What you get

  • A 1 hour drawing date with me, Rose Wintergreen.

  • I will take you to one of my favourite drawing locations, and share my process (including how I talk back to my inner bully, Ursula, when she gets too big for her boots, as well as art techniques).

  • We will draw side by side, each creating our own drawings to take home afterwards.

  • Each drawing date is capped to a maximum of 6 people.

  • All materials provided.

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I had a great experience!

I wasn’t making art before I had a drawing date with Rose. I didn’t know where to start. When art is so often a solitary pursuit it is so nice to share the experience with someone so you can learn and teach one another. I have lovely memories from this. – Jacqueline, 28, teacher



What if I’ve never drawn before?

Fabulous! You have less head-crap to unlearn about how to draw freely. You’ll be able to teach me!

What if I want to learn how to draw “properly”?

This is not for you. There are many other places to get taught how to critically assess your skills and techniques and to learn how to draw technically correct, proportional art that is a realistic representation of the subject. These drawing dates are about learning how to find freedom from your inner critic and enjoy the process, regardless of how it turns out.

What if it’s bad weather?

I have back up locations sorted. Meeting places are chosen with this in mind.

What if I already know how to draw, is it okay to come?

Of course! So long as you don’t try to tell others how they “should” be drawing. These drawing dates are all about exploring creative play and freedom.

Is it okay to bring children?

Drawing Dates are currently limited to people aged 18 years and over.

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I enjoyed it. It was relaxing.

It made art feel more accessible. It made me feel more comfortable about making art. Give it a go, you might be surprised! – Adam, 47, public servant


More about Rose

I’ve done a lot of different things, including working as a creativity coach, marketing manager, statistician, research officer, support worker, and recording and touring as a professional recording artist. The pattern: I have always pushed myself beyond my limits because I didn’t know how to protect myself from my inner critic, Ursula, who always told me I needed to do more, no matter how many hours I had already put in, and that I was never going to achieve enough, or be good enough.

It was only after suffering a spectacular health crash - my body would literally not let me go on - after touring nationally three times with my last record release (I was the tour manager, the booking agent, the publicist, performer and artist manager, whilst also running another business) that I finally realised I couldn’t live that way anymore.

Rose Wintergreen, photo by Michelle @mission_tell

Rose Wintergreen, photo by Michelle @mission_tell

I found my way back to colour and drawing by accident. People kept giving me mindful colouring in books. I didn’t want to colour in, I wanted to get shit done! But I was too burnt out to do anything but rest.

I gave in out of desperation and started colouring. Over time, I started doing my own drawings, and I realised making time to sit and play with colour and line just for the sake of it was bringing me peace and freedom from Ursula’s voice, especially if I reminded myself “I am not trying to be good, I am finding new ways to play with colour and shapes and lines”.

Now I’m a prolific artist creating a brighter world with joyful abstract drawings and paintings. I haven’t conquered Ursula so much as learned how to have a loving relationship with her.

People often ask why I use so many experimental techniques in my art, like drawing without looking at the page, or drawing moving objects or music. It’s one of the ways I’ve learned to loosen Ursula’s grip and claim my human right to create and express just for the joy of the process.

It is your human right to create and express just for the joy of it. I’m passionate about sharing my techniques so you can find relief from your inner Ursula and come home to yourself. It makes your world brighter when you do this, even if you don’t ever share what you make with others. The energy is contagious, I promise. Let’s make the world a brighter place together!


Terms and conditions

Refund Policy

Please choose carefully as fees are non-refundable. Refunds of workshop fees will only be given if the Drawing Date is cancelled. Rose Wintergreen cannot accept responsibility for changes to attendee’s personal circumstances that prevent attendance.


Drawing Dates operate in all weather. I may amend the location if weather circumstances require. Drawing Dates may be cancelled due to extreme weather by mutual agreement when there are severe weather warnings issued by the Bureau of Meteorology for the planned location of the Drawing Date. No costs are incurred by participants if this occurs.

Health & Safety

Covered shoes must be worn for all Drawing Dates. Please also bring whatever you need to make yourself comfortable, e.g. a small cushion or collapsible chair if you are not able to sit on the ground, sunscreen and a hat for sun protection, an umbrella if it is raining, and water to stay hydrated.


Drawing Dates are a place to feel safe and relaxed. Please do not take photos of any other attendees, or anyone else’s drawings without first asking for consent. You are, however, encouraged to take photos of Rose Wintergreen, yourself and your own drawings during the workshop if you would like. If you decide to post these to social media, you can use the hashtag #drawwithRose

If you verbally consent to having your photo taken by Rose Wintergreen on the day, you also grant permission for Rose Wintergreen to use it for marketing material to promote future Drawing Dates and affiliated activities.


Any information maintained by Rose Wintergreen, for example, email correspondence or booking forms, is gathered and used solely for the conduct of Rose Wintergreen, will be kept securely and will not be divulged shared or sold to a third party.