MS Paint Portraiture

MS Paint Portraiture

Sometimes when Emmy and I are just hanging out, she’ll load up MS Paint and draw terrible pictures of me. I say terrible, because she has an exceptional talent for creating images of me that are incredibly unflattering (she’s actually really good at pixel art). Admittedly they’re also incredibly entertaining. When she asked me to draw her as well (with similarly amusing results), it was apparent this had the makings of another date idea.

As far as at-home dates go, this one’s got a lot going for it. It’s fun, flexible, and costs basically nothing. Plus you can do it remotely over your preferred method of video chat. So if you’re still in lockdown, don’t let that get you down!

What you’ll need:

  • 1x computer, tablet or smartphone each (or you can share if you don’t mind taking turns)
  • Basic image editing software (MS Paint preferred)
  • An internet connection and video chat app if you’re dating remotely
  • A sense of humour (essential)
  • Artistic talent (optional, as always)

The premise is fairly simple: You and your partner draw portraits of each other in MS Paint. How do you make a date out of that? Pretty easy actually. For example:

One or two practice drawings at 5-10 minutes each. One main drawing each at say, 30 to 60 minutes. Plus, time in between discussing the finer points of the hilarious renditions you’ve made of each other…

Or you could:

Do a series of drawings in different styles, maybe 10-20 minutes each. Depending how many drawings you do, and how much time you spend discussing them, you could easily eat up a decent slab of time..

You may want to set a timer to keep things flowing, or just see where the activity takes you.

Why MS Paint?

For starters, most Windows PCs already have it installed. Plus it’s familiar to almost anyone who’s used a computer, and carries a lot of nostalgia. It’s so popular that Microsoft changed their mind about retiring it. Many of us 80’s and 90’s kids have fond memories of creating pixelated graffiti with the spray paint tool, and being amazed at being able to fill in vast spaces of colour with the paint can tool. Although the modern version doesn’t have quite the same functionality, the classic Windows 95 version is available here online.

And I mean, sure, you could do the same thing with paper and pencils or other traditional artistic implements. But that requires more effort, presents greater margin for error (you can’t hit the “Undo” button on paper), and may make you more prone to perfectionism. It’s a very romantic notion to want to recreate your partner’s visage with photo realistic accuracy. But that’s beside the point of this date idea. MS Paint has its limitations, and the point is to have fun and be creative within those limitations. You’re not likely to produce a masterpiece in the space of an evening, but you can create a somewhat nostalgic and amusing tribute to that special person in your life.

“Plus it’s great for stress relief”, says Emmy

Stylistic Preferences

The other thing about using MS Paint’s limitations, is that they lend themselves to more simplistic, cartoonish styles. Don’t be afraid to borrow artistic stylings from your favourite media. For example, you could draw each other in the style of your favourite:

  • Anime/Manga 
  • Classic cartoons
  • Comic books
  • Illustrators
  • Videogames (We did Animal Crossing at one point)
  • Anything else you can think of!

Or just wing it. Use your own artistic interpretation. Play around with the tools at your disposal, it’s all part of the fun! 

The Finer Details

When drawing another person — especially in a simplified style — you’re more likely to focus on their most prominent features. Now before you go making caricatures of each other, make sure you’re both cool with it first. Unless you think your relationship can handle it, be wary about amplifying any features they’re overly sensitive about. In some ways this is as much an exercise in trust as it is an artistic exercise. 

Your levels of artistic talent may also differ, so do your best not to be judgemental. In this exercise, personal expression is much more important than technical skill. That said, if you’re crap at drawing (and you know it), just do your worst. You’ll both get a good laugh out of it! Another way to embrace limited art skill, is to draw while exclusively looking at your model’s face, not the screen. This will either result in barely recognisable scrawling, or a slice of surrealist-minimalist intrigue. Either way, it’s entertaining.

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