We all have a little voice inside our heads telling us that we suck. “It’s true, the inner critic is an asshole,” says Dov Tiefenbach, the splendidly-named actor whose role as Benny in Pretend We’re Kissing required him to actually find a tone for that corrosive interior monologue.

Tiefenbach’s Benny is a lovable dweeb with relationship woes, a healthy portion of self-loathing, and a private colour commentary that won’t let up—most amusingly as he pursues the more freewheeling Jordan (Tommie-Amber Pirie) through a beautifully lit Toronto. As a determined “non-rom-com”, Pretend We’re Kissing, opening Friday (April 3), could have been a drag. Instead, thanks to Tiefenbach’s performance and some smart writing from first time director Matt Sadowski, it’s a bittersweet delight.

“I think we really worked hard at finding the logic in the character, which maybe makes him sympathetic,” offers Tiefenbach, calling the Straight from Hogtown. “I think in a lot of films, there’s an idea of the character, and the character acts based on that idea, and so you feel a little alienated from him. Matt and I worked very hard on going through every line, and every moment of the film, trying to understand why Benny does what he does. Not only in the character, but in our own lives. We tried to relate it to ourselves.”

The attention to detail pays off, and so does the film’s unsentimental take on romance. Jordan’s starry-eyed belief in “the one” is every bit as hobbling as Benny’s chronic shame, which gives Pretend We’re Kissing the ring of truth. Benny has also been lumbered with an unwanted roommate; hardly unusual for the 20-something set depicted in the film until you take into account that she’s an indoor nudist played by Zoë Kravitz, and that she spends the first 10 minutes of the movie completely naked. If Sadowski is straining credibility with the set-up (Benny’s not interested—she’s a “dirty hippy”), it’s probably worth pointing out that it’s also based in reality, somewhat.

“Except it wasn’t a couch, I actually had an extra bed,” explains Tiefenbach, who really did let the younger Kravitz (daughter of Lenny and Lisa Bonet) crash at his place when he was living in L.A. “It wasn’t as cramped, but there are definitely parallels. You could say that I’m very uptight and Zoë Kravitz isn’t very uptight, and the dynamic of living together was very similar. I think we were making fun of ourselves, you know?”

Tiefenbach did his time in Los Angeles after establishing a career in Canada in his teens. He’s a New York resident now, which offers another neat parallel to the film. Check the style book Tumblr on the Pretend We’re Kissing website, and you’ll find a still from Annie Hall. It probably hasn’t escaped everyone’s notice that Benny is wearing Alvy Singer’s jacket.

“I grew up watching Woody Allen, and idolizing him, and I think we might have both allowed a Woody Allen influence into the film maybe more than we should have,” Tiefenbach states with a chuckle. “I think we both hope that there’s still enough truth; that Benny is his own character.”

Tiefenbach needn’t worry. In any event, Annie Hall isn’t the only New York-based film classic from the ‘70s that features a green army coat.

“Yeah,” exclaims Tiefenbach, “it’s a Travis Bickle jacket, not an Alvy Singer jacket!”