Debra DiGiovanni came to Toronto to become a fashion illustrator and thinks that she probably would have ended up as a teacher had she not found her true love — stand-up comedy. As one of the judges on MuchMusic’s Video On Trial and CBC’s The Debaters, she is keeping busy enough without doing stand-up. However, this November she is touring Ontario with her Single Awkward Female Show, inviting audiences to recognize themselves in her tales of misadventures. When The Varsity caught up with her on the phone, she had just landed in Calgary earlier that morning. She is coming to Toronto’s Panasonic Theatre this Sunday, November 13.

The Varsity: I saw on Twitter that you squeezed in a nap before our interview — does it get hard to muster up enough energy every night to be funny?
Debra DiGiovanni: You know, it actually does. I love what I am doing and I am so lucky, but at the same time, you travel a lot, and when you fly a lot, you tend to get sick all the time and you are by yourself. But the lucky thing is you get to a club and you have all these people there, and the energy just helps. I’m pretty lucky, but it’s less glamorous than you think.

TV: You are doing a mini-Ontario tour this November called Single Awkward Female Show. Tell me about that.
DD: Yes, I am doing a DVD this year with my management. And we thought it was just a funny name, kind of a thumbs up for what I do — the gist of my show, really. I’m pretty excited; this is the first tour I have ever done by myself! It’s fabulous but it’s also scary. It is a lot of pressure, but I’m moving forward and that is good. Always onward!

TV: What has been your single most awkward moment?
DD: Oh gosh (laughs). I have a lot, to be honest. I am not that smooth; my friends make fun of me all the time. I had a guy come up to me after a show and I guess he wanted to talk to me, but I had no idea. He was trying to buy me a drink but I don’t drink and I turned away and he was like, “Er … do you want a bottle of water…?” and I said “No, thanks” and he looked at me like “Really? Are you really doing this?” and all my friends were in the corner of the room looking at me. That’s just me, I really have no concept at all. Like flirting, I really don’t know what happens when I try to flirt.

TV: Well, in recent years, “awkward” has become the new “cool.” We can see that in popular TV shows, nerd culture, etc.
DD: Exactly, the weirdo is sort of cool right now. It’s a new trend, especially in comedy as well. It’s like the weirdo is the new anti-hero.

TV: Lots of your comedy is based on poking fun at yourself, pointing out your insecurities. Is it hard to make self-deprecating jokes?
DD: I think it’s all about identifying with my audience. We have all been single and awkward at one point in our lives. That just seems to be where people go click and say “Oh, I get it.” And that’s one of the things that really connects the audience with the performer. Often people will come up to me after a show and tell me that I remind them of their babysitter when they were little or their favourite teacher in grade school. That’s how you create fans, you know, make connections where people remember your name.

TV: Do you think audiences have different expectations for female stand-up comedians? Would you say it’s harder to convince them that girls are funny?
DD: It can be. There is always a bit of a struggle because when men see a woman on stage, they associate her with their mother, their sister, their daughter. They are more protective. There are certain groups of men that I find a little difficult to sway. They’ll be like “Whoa, there is a woman on the stage?!”

TV: “Not sliding down a pole?!”
DD: Yeah, and you often have that guy, you know, sitting across from you, arms crossed. But when you get a chuckle out of him, it is the greatest thing in the world. And it’s always those guys that will come up to you after the show and say “Yo, you are pretty funny for a girl…” Thank you very much (laughs)!

TV: How did you get into stand-up comedy? Was there a specific event or point in your life when you knew you would pursue this as a career?
DD: In high school, I was always the funny one; I always made my friends laugh. And when I went to college and had part-time jobs, everyone said I should be performing but I was just like “Oh whatever,” didn’t really think about it. But I would hear it over and over again and it got me thinking that maybe it’s true, maybe I could do this. And then, luckily, Humber College started their Comedy: Writing and Performance program in 1999, and I took that. I went through first year with honours and it was fabulous. I got to learn about screenplay writing, improv and acting — it was the first time I had ever gone on stage. It just worked; I immediately loved it. It was true love. And I knew stand-up was going to be it, my area of expertise.

So I did that but had a day job. Probably the year that I went to Just For Laughs for the first time and Russell Peters invited me to open for him on his tour, in 2005, was the moment I realized I could do this for a living. It was great! I was able to quit my job and — knock on wood — I have not had a day job since.

TV: You have a lot going on; tell me about some of the projects you are currently involved in.
DD: I am working a lot more in the States now, which is wonderful. It’s very hard but you have to continually knock on the door. Right now, I am working on getting some more TV projects off the ground. I love, love, love working on Video On Trial but there has got to be “the next show” and that is what we are working on right now. Again, it’s all about progress, keep moving up. And I would like to have more control with my next show. On Video On Trial, it is all up to the editors what they cut and what they use. Sometimes I watch an episode and I think “Hey, I made a really funny comment there — where is that?”

I also went to the UK for the first time this year, so I’m reaching out a little bit now.

TV: Did you do stand-up there?
DD: Yeah, I did. I was in Scotland and England, and it was a very new experience.

TV: I’m sure the audience was different. 
DD: Well, their comedy style is different; they are somewhat more wary than North America. It’s a little more difficult. Also, their comedy culture is big on storytelling and those kinds of jokes. In the end it’s just a new place, and you have fun and try something new.

TV: What are the main differences between working in TV and doing stand-up?
DD: On camera, you just reach so many more people. But you can’t control editing, and I think for comedians, that’s the hardest part. On stage we can say whatever we want. When you get on TV, you have no control over what they put in and what they don’t put in. So, complete control is what is missing when I work in TV. But hopefully one day, I’ll have the final say.