I Cope with the Insanity of Online Dating by Illustrating the Men Who Hit on Me

On my Instagram account, I post drawings of their faces, accompanied by the first messages they sent me.

For the first few months of my online dating adventure, I was a total wreck. I created profiles, deleted profiles, created profiles, deleted photos, took new photos, sweated it out, and then deleted everything altogether. Create, delete, dry heave, repeat.

Is that extreme? I dunno. I had been with the same person for about a decade and we got together pre-Tinder/Match/OkCupid, so, like — basically I had no idea what I was doing (and still don't). What exactly is "dating" anyway?!

Critical to surviving online dating is having people to talk to about it. I wasn't the only one hitting up against issues of identity, technology, communication, love, and lust. We all have great stories and collections of screencaps of the best/worst. Often the most rewarding part about online dating is swapping stories.

What I found so interesting was how similar and how different our experiences could be. Me and my gal pals were all getting called "hun" and "sexy" and "baby," but at times, I was getting messages that were completely different from my friends who were white, brown, and black. I recognized the sad lack of sexual diversity, and the classic heteronormative patterns where men pursue and women wait to be approached. My inbox was full of messages sounding like cover letters for job applications and requests from men who wanted to try me out, like a test drive or something transactional, following the language of economy.

I wanted to encourage more conversation, not only with my BFFs, but with as many people as I could. Within the parameters of these pretty basic apps were a lot of huge issues on how we communicate, and who, how, and what we desire romantically.

Being an Asian in Canada, I grew up being asked where I was really from all the time. I was supposed to be good at math but bad at driving. I never forgot that I was Asian — and not white — because people would always make sure to remind me.

But what made online dating so stressful was how it added a whole new dimension to my Asian-ness. A lot of the messages I received were like "hey girl" or "ur sexy wanna chat" or "are you into threesomes?" But then other messages were darker: single-man-seeks-mail-order-bride-slash-wartime-comfort-woman kinda feel. It wasn't just about hooking up or making friends or meeting some dreamy forever guy. Suddenly all the red flags were up and I'm like, Oh riiiight: I'm a fetish.

Getting angry isn't really, like, a thing. Outwardly, anyway. Asians are docile — submissive, right? Dominant ideas about gender and what it means to be Asian, to be black, to be brown, are continually being challenged by the emergence of strong intersectional feminist voices. We are changing the narrative, and I found myself asking, "What can I do?" But change is slow. While I strive to change, I continually struggle to express my opinions, needs, desires, and emotions like OMG anger. In fact, most of the time, I can't even access it.

It wasn't quite "anger" I was feeling about the messages I was getting anyway. It was more like WTF? and how can I turn this on its head? How can this transform from a disturbing subjective experience to a cultural, collective one? What is this big social experiment, and how are we all going to navigate it?

There are countless Instagram and Tumblr sites dedicated to documenting the online dating experience: fetishes, raunchy propositions, terrible conversations, and of course, shoulder animals and hot people jumping. They're funny, they're sad, and they're maddening. For the most part, they are all selected extremes: how stupid someone is, how rude, how persistent, how pathetic, how sexy, how sexist, how horrifying. At their best, these sites call out oppression and create awareness. They can be a great way to get dating advice and support. The best ones make you laugh. But at their worst, they become a race to the bottom of how bad it can get. Though I believe that there needs to be space to rage about all of this, I found some of the sites and forums to be excessively toxic, divisive, and unproductive, ending up with just a whole lot of hating.

I wanted to take a different approach to documenting. Being an illustrator, of course it made sense that I would paint caricatures of the men who were messaging me. I wanted to draw attention to their faces and their expressions, and directly connect them to the first lines they wrote to me. I've been posting them all on an Instagram account I call @ok_cucumber.

Painting someone's face is an intimate act; I spent so much time just staring at their photos and following the contours of their hair, lips, and jawlines, trying to capture the look in their eyes, their vibe. I thought about the line they sent me and the face that sent it. In the time it took me to paint one face, I could have left- or right-swiped and judged my compatibility with hundreds of people.

Using illustration was also way of creating distance between the work and the real men who sent them. I didn't want to out anyone or humiliate anyone; I wanted to re-create them as characters on a search for human connection online — ones that we could relate to, or that we couldn't relate to, but had encountered along the way. In kind of a flip, my hope was that by translating profile photos into illustrations, we might spend more time with them, and they would actually become more real, more human, and less like products that we are browsing or shopping for.

Another way to humanize the whole experience was to include everything. I decided to draw the most banal messages — "Hi," "Hey how was ur day?" and "Hello sexy" — along with the most troubling: "A slut is what I am in the mood for" or "Do you like big white cock?" All of the spelling, punctuation, and emojis are as they were when I received them. The same messages recur over and over, but the faces sending them are different.

Ultimately, my goal was to connect with more people and to expand my experience. To gain understanding and to explore a bigger, clearer picture of the modern culture of love and dating. I'm excited about it, and I look forward to more people sharing their stories. I want to talk about what power relations within dating, relationships, and desire look like, and how to disrupt that.

And while we are at it, why not make this all about love? I've loved every moment of this project; it has connected me to so many people in the best way possible: through laughter and stories. I hope you enjoy it, too.