Dating With Depression Sucks

"When you're talking depression," explains Safra in the web cartoon People Watching, "it's a whole thing of not feeling like there's a point to doing anything because you're so shitty or the world is so shitty, and you can't stop telling yourself that, even though you know it's not true." The scene is a first date at what looks like a hipster eatery, and the characters haven't even ordered drinks yet. Indie rock is playing in the background and Safra and Jeremy banter about mushrooms and nerdcore music between attempts to articulate the existential dread they're feeling.

People Watching, the new animated series from a Toronto cartoonist who goes by the pseudonym Winston Rowntree, is about very self-aware young adults trying to create a connection. It mirrors the dialogue-heavy style of his web comic Subnormality, which is also published on Cracked.com. In conversation, Rowntree was less expressive than his characters, pausing often and answering questions about himself with a second-person "you" or a response about what "people" commonly feel. I couldn't find many details about you online. 
I'm not really about sharing details about myself. I don't do Twitter or anything. I don't know. It doesn't occur naturally to me to talk about myself. I just sit behind a pseudonym and let the work speak for itself. That's the most important thing to me.

All your work is very text heavy. Do you start with just a long script?
Yeah, always a script. I just enjoy the writing part. I produce a lot of text and I go from there.

I watched the first three People Watching episodes. How did you come up with all those characters?
I wanted to focus on characters where their outward appearance didn't match what was inside. They all have some duality to them. That's where I started from in terms of designing the characters. I gradually came up with how they looked digitally. A lot of it was arbitrary choices, because I like to start with an arbitrary set of characteristics, as opposed to deliberately choosing what someone looks like. It was a combination of random choice and people whose inner lives didn't reach their outlines.

I think they are self-aware in ways that people in their late 20s and early 30s are right now. Did you draw that from people in your own age cohort?
Oh, yeah, definitely on myself and people I know. A lot of people I know are in the arts and none of us make any money. When we were kids we all saw a version of what adulthood would be and then by the time [we grew up] was precluded by the world evolving. That is what it is.

In the third episode, it seems like the characters are working to express something, they're trying to tell each other there's something wrong with them, in a polite way, and to expect that if they continue. Is that a conversation you've had with yourself? 
It's a big thing that I worry about. I don't get myself out there that much because of various insecurities that are expressed in that video. A lot was taken from my own head. You judge yourself more than anyone else could judge you. You assume other people wouldn't accept you, even though they [probably] would. It's all drawn from reality.

They also talk about this choice that's unique to online dating, disclosure vs. privacy. Is that a choice you have had to face? 
Yeah, if I am going to write an online dating profile, it's always, "How much am I going to say?" It's always my instinct to just write it so you don't give anyone any ideas later on. That can be a bad idea. That's a thing I see a lot of people have issues with.

Does being a writer make you better at creating an online dating profile and communicating online? 
"Better?" I don't know. I don't know if anyone can be "better" at dating, online or otherwise. It depends on what kind of writer you are. One of my reasons for writing is to communicate personal truths. You would hope that would lead to you being better at that in your personal life, but nothing is that cut and dry.

In episode three, we see a personification of the woman's depression as this mustached villain. As a cartoonist, how did you decide how a human representation of depression should look? 
It was just a humorous idea to update the stereotypical villain, but the key was to this was someone you're letting in: They belong in your apartment and they look like you. Eventually, you realize they're the bad guy. You've been listening to someone terrible. So it was a combination of a villain and someone you think you should be listening to because they look like you. It's also important it that is was an external voice, as opposed to thinking it's you.

It also seems like your characters are coming to grips with the banal awfulness of their world. Is that something you have faced or people you know have faced? 
I think everybody does to some extent. How would you answer that?

I don't know. I don't know if the world is awful. I think there are certain truths to accept. Our generation will never have it as good as our parents did economically and the world is confusing. I don't think I've reached the level of nihilism of some of your characters, particularly the exotic dancer from episodes one and two. They really reminded me of Douglas Coupland's characters in their struggles with limitations. Have you read him much?
I haven't read him. I haven't read anyone in a while. I'm surprisingly poorly read.

It seems like Safra spends all of her effort on the date on her own anxiety. She never gets to the part where she asks if this could be a workable relationship. That's certainly an experience I have had on a first date. Is that an experience you have had? 
Yeah, a lot of people, I think, are insecure. There's a lot of pressure to be successful in a certain way. We're very insecure about the things we perceive as being unacceptable to others. In fact, we wouldn't judge others for the things we judge ourselves for. I think a lot of people reflexively apologize for things they shouldn't apologize for. We don't see our flaws portrayed in the media so we assume that people don't accept them. I just try to write things where people can see other people with the same kind of flaws and maybe that will help in some way.

Also, no other generation has done as many first dates as we have. Our grandparents just married whoever they were standing next to when they turned 22. I wonder if it's normal or healthy to be evaluated so many times and evaluate so many other people during a 15-year span. 
Yeah, that's a good question. Yeah, my grandparents were random people who didn't even like each other and then were married for however many decades. My parents were slightly pickier, and now there's a lot of pressure to find your exact right path in life, your exact right job, your exact right partner. There is a lot more choice. It's good that we're not just marrying the first person we come across. I think that has good and bad to it. The people I know who are in happy relationships definitely are happy. I don't know if [all that dating] is healthy or not but people can still find love.

You said you don't see your flaws portrayed in other media. Are your cartoons a correction of that?
I think it would have been a bolder choice five or ten years ago. But I think a lot of people have done a good job portraying what depression is. It's a big thing on the internet. There is a lot of comic strips and blogs explaining that experience. I think it's part of a trend, a good trend. Five or ten years ago, I didn't know what depression was, despite having it, and now people understand it's a thing.