Starring Dov Tiefenbach and Tommie-Amber Pirie. Rated 14A.

How much you enjoy Pretend We’re Kissing is going to depend on how irritating you find its main character, Benny. Think Woody Allen as a hipster nerd who works as a posterer and wears a khaki parka and tuque. Oh yeah, and he’s addicted to nasal spray—always an attractive vice.

His neuroticisms in Matt Sadowski’s stylishly shot, resolutely indie film run as an inner monologue the audience can actually hear. Benny (Dov Tiefenbach) takes negative self-talk to a whole new level. (“Go over. Go over right now! Oh God, I’m so nervous.”)

He can’t even work up the nerve to kick out his freeloading roommate Autumn (Zoë Kravitz), a New Age nudist who’s also a self-diagnosed agoraphobic.

Benny’s lonely life starts to look up when he spends a magical night with the uninhibited Jordan (Tommie-Amber Pirie) stuck on Toronto Island after missing the last ferry. But can he drag himself out of his head for long enough to make it work?

No complaints about the acting here, which manages to be quirky yet naturalisitic. Sadowski provides some dry laughs too, whether it’s the look on our leading loser’s face when a woman grabs the last two lemons at the grocer or Autumn repeatedly demanding he “Stop being a Benny!”

And anyone who’s ever spent much time in Hogtown is going to appreciate Sadowski’s love letter to old-school T.O., complete with nods to the Cameron, the Rex, the Drake, and a landscape of diners and bargain centres.

But they’ll also have to endure one of the most cringe-inducing, extended sex scenes in recent memory. As you might imagine, the insecure Benny is no Eros in the sack.

In fact, Pretend We’re Kissing, the ultimate non-rom-com, works that painfully awkward vibe throughout, becoming a comical string of missed chances and anticlimaxes. Whether you can deal with that may come down to how much humour you can find in authentic discomfort—and, probably, how close it hits to home.