Ok, Stupid: Hand-Drawn Selfies and Online Dating


Dating as a twentysomething feminist survivor in the age of selfie culture and social media is no joke. The personal is still very much political. We are living in an unprecedented moment of transition in interpersonal relationships, due to a combination of economic, social and technological transformation.


I was born in 1984, and have peers who can tell stories of finding lifelong friends or their first teenage loves on Makeout Club, Friendster, and MySpace. Long before our current era of social media and smartphones, whether we accessed bulky computers from home, our friends' houses, or the library, the narratives of many of our lives held plot arcs marked by instant messages and emails. Coming of age in a moment when the world began to discover just how big and just how small it was offered deeply exhilarating and frightening prospects.

In 2011, shortly after the end of an unhealthy long-term relationship, I was engaged in a raucous, wine-amplified conversation with a group of highly accomplished, intelligent, creative sister-friends. Mortifying, hilarious stories of misadventures in online dating kept us cycling in peels of storytelling and laughter. Afterward, with the intention of starting some kind of collaborative comic, I joined OkCupid to begin what I told myself was simply a sociological and creative experiment.

The plan was simple. I'd join OkCupid and go on a couple dates, making notes of funny or interesting stories to build upon later. So many things about online dating were strange and fascinating to me. The two-step of self-objectification and commodification, as OkCupid is essentially a kind of Amazon for potential partners. The slight shame so many people have about choosing to join in the first place. (Just see how many times people refer to having an OkCupid account as the "one private thing" they are willing to admit to). The hope that keeps people coming back to check their messages, even after receiving frustrating, insulting, gross and downright ridiculous advances. As a woman and a survivor of sexual assaults, there was the fear of "stranger danger" and navigating unexpected triggers when confronted with unsettling gender dynamics or other vulnerable moments.

Shortly after deciding to start the project, I went on a particularly disappointing date after a long day of working with brilliant young people. For many years now, I have encouraged the young people I collaborate with to explore and express their perceptions of their own lived experiences through art and writing. For many, this can be really intimidating at first. It's risky to expose yourself, to share a messy process of understanding when you are still very much making your own sense of the world, let alone discovering yourself.


I came home after this disappointing date, sat down at my drawing desk, and reflected on my day. Suddenly, it dawned on me that I had been encouraging young people to be brave in their practice in a way that I was not. Most of my art has long vacillated between political/community collaboration, social commentary and occasional silliness. My work talked about things I saw, things I knew and things I experienced, but rarely did I make work about my own life to share with others. I assumed no one would be interested. I only very rarely made self-portraits, mostly when I needed to draw and felt a little uninspired. Mostly, I found myself feeling narcissistic when I tried.

The night of my first disappointing date, I took a picture of myself with my webcam and started the "Ok, Stupid" series and have been working on it little by little for the past three years. I do it for me, because it gives me room to process, reflect and confront myself. I lost interest in finding responsible ways of recounting actual dates, because I was not interested in potentially or non-consensually exposing anyone. (Oooh, but get a few drinks in me with my crew and I got stories for daaaaays.)

Whenever I'm working on or have finished a drawing I particularly enjoyed making, I post it on social media as a means to instigate dialogue. I try to camouflage the drawings to pass in selfie culture. I also try to be transparent about my process because so often we just see the finished products of things, and I am interested in the documentation of the process as part of the process itself.

Over time, the project has progressed, and become more of a series that helps me meditate on my own very particular, personal relationship as a woman to the larger world around me. In doing the work, I have grown up, and so has the project itself.

Now, "Ok, Stupid" is an ongoing series of drawn self-portraits inspired by self-representation of women in the digital age and online dating as a young, working-class feminist survivor navigating a surveillance/exhibition culture. The series plays with questions of the gaze, and looks to the intersection between both the history of women's self-portraiture and today's selfie culture, as well as confessional writing and status updates. There are drawings about crushes, sex, frustration and introspection. There are a lot of pictures of me.




Most of all, this series is inspired by all of the people in my life who are trying to make sense of our longing for intimacy, partnership, love and acceptance in a contradictory cultural moment of dissociation, loneliness and hyper-connectivity. I've had frustrating, awkward, frightening, hilarious, anticlimactic, silly and lusty dates. But I have also shared some sincere moments of innocent (and sometimes less innocent) intimacy, and surprisingly, I have made some really great friends.

Above all, I've learned the value of self-discovery and self-exploration in relationship to other people who are putting themselves out there, online, in the pursuit of some kind of meaningful connection. There's a parallel between the challenge of having to reciprocally disclose and perform on a first date with a semi-random human from the internet and the drawings that I make afterward, quietly, reflective, in solitude.

I don't go on that many OkCupid dates (or that many dates in general) anymore, and I didn't find loooooove on the Internet. But the beauty of this whole experience has been that in my intention to objectively, intellectually approach today's search for intimacy, I became more committed to my practice and had to more deeply confront and converse with myself. I think this makes me better able to love another person fully, and more prepared to receive loving partnership if and when it arrives.

Either way, I'll be at my drawing desk, trying to figure stuff out.

Are you interested in Mensen drawing the portrait of you or someone you love? Contact her at msmensen@gmail.com.