Ever been on an online date so painfully bad you just had to phone a friend to process the horror?

Back in 2015, I started turning those exact cinematic dating disasters into art form. Under my pen name, Fig, I began capturing the absolute lows of my online dating life in quick, black-and-white style illustrations.

It was a low-key side project born out of pure shits and giggles. I’d store notes on my phone right after a date, draw the guy on paper with a UniPen or Muji ink pen, finalise it in Illustrator, and export it to Instagram.

I called it Fig’s Dating Life. It was candid, bittersweet, and mostly just a way to laugh so I wouldn’t cry.

Then, a global publisher knocked on my door.

From side hustle to the printing press

A few years back, there was a bit of industry chatter about turning the drawings into something bigger, but nothing really eventuated. The thought of it honestly freaked me out anyway. No-one knew who I was. Was I really that funny?

But out of nowhere, BrownTrout Publishers reached out. They wanted to see the old calendar mock-up I’d put together years ago. I did a few edits, sent it off, and then… total radio silence.

Until my phone rang.

The publisher told me three simple words: “It’s going ahead.”

I replied with the only word my brain could physically muster: “Fuck!”

The commercial compromise and designer workarounds

Getting a calendar published isn’t just a straight line from Instagram to the printer; it goes through a massive amount of iteration with the publisher and a bunch of stockists to make it retail-ready.

One of the biggest hurdles for me was the name. It was always supposed to be called Fig’s Dating Life. But the powers that be – the publisher and the retailers – insisted on changing it to Swipe Left. Apparently, it was “more commercial.” To be honest, it hurt a bit to let go of the original title, but I chose to trust their industry expertise and rolled with it.

From there, I essentially illustrated and hand-crafted the entire thing. But because it was so text-heavy, I hit a wall. At one point, I got so utterly sick of manually rewriting content and hand-lettering changes that I just decided to turn my own handwriting into a fully functional digital font. Oof! It made life a million times easier to just hit backspace on my keyboard rather than rewriting a whole section on paper to scan and drop back into the layouts.

I also scattered actual online dating tips throughout the monthly grids. Because I wanted the advice to be genuinely helpful (and not just cynical), I actually had my psychologist proof them all to make sure they were totally kosher and emotionally sound.

The project blueprint

• The Concept: A 12-month snapshot of real online dating culture, featuring eleven hilarious, painfully awkward dates.
• The Lineup: Infamous characters like Pash Rash Boy (Spoiler: the answer to “Can I kiss you?” was a firm no) and Booty Boy (featuring an incoming call illustration at 4:00 am).
• The Interactive Twist: Because I wanted the audience to feel part of the process, I left an space in December for people to draw their own terrible date.

Hustling outside the wholesale box

Here’s the thing about working with a wholesale publisher: they get you onto the big retail shelves, but the actual grassroots marketing? That was entirely on me. If I wanted people to actually buy this thing, I had to go hard.

So, I leaned heavily into social media marketing. I started posting regularly and hosting Instagram Lives where I would literally draw people’s horrific dating stories in real time. It was raw, hilarious, and connected me directly with a community of fellow online daters who just wanted to feel seen.

But my absolute favourite part of the entire journey? The packing process.

I set up my own online store for my own network to buy the calendars, and I wanted the unboxing experience to be an absolute vibe. I sourced eco-friendly packaging to keep things sustainable, printed custom ‘Thank You’ cards, and then decided to elevate the comedy.

Every single order packed by hand in my studio included:

• A custom ‘Thank You’ card.
• A little bag of dick-shaped candy I meticulously sourced.
• A healthy, unhinged handful of dick confetti tucked right into the package.

There is nothing quite like the joy of knowing a customer opened their mail only to get a glorious, unexpected sprinkling of dicks all over their living room floor. I loved every single second of packing those orders.

 

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The reality of “making it”

It is a genuinely wild feeling to realise your personal dating horror stories are being printed, packed, and shipped for strangers to stare at on their walls for an entire year.

Navigating the commercial publishing world as an independent designer was a massive learning curve. Suddenly, my tiny Instagram doodles were being scrutinised for retail price points ($20.00 AUD / $24.99 NZD), global barcodes, and official sales sheets.

If this project taught me anything, it’s that there is massive value in your weirdest, most vulnerable passion projects. You don’t need a massive corporate machine to create something that connects with people – you just need to be honest, a little bit brave, and willing to mail a bag of candy dicks to a stranger.