This new webseries satirizes the existential hellscape of dating in Toronto

If you're single, Miss Misery might hit a little too close to home.

If you're single, Miss Misery might hit a little too close to home

Miss Misery. (One Ten Productions)

Are you in an open relationship? Probably like maybe, right? What was once a scandalous lifestyle choice relegated to the back pages of "Savage Love" has entered the mainstream. No longer for swingers dipping their hand into a glass bowl at a 1970s key party, polyamory is beginning to seem like the most sensible choice for overextended millennials looking for more than one person to fulfil their emotional and sexual needs. 

A new web series, Miss Misery, which you can stream now, strikes just the right note in identifying the humour and complexities that come with adopting a polyamorous lifestyle. The series follows a married couple in their late 20s named Jay (series co-creator Steve Thomas, a fiction writer in Toronto) and Amy (musician and writer Aley Waterman) as they make the decision to "open things up," after they admit the sexual chemistry in their relationship has flatlined.

Amy confides this to her best friend Lee (co-creator, writer/filmmaker Jade Blair) who finds herself in the awkward position of falling for Jay and Amy's downstairs neighbour Sebastian, who is all too happy to sleep with her, as long he can maintain the boundaries in his own open relationship. A series of sexual exploits, painful realizations, and awkward Tinder dates at iconic Toronto locales soon ensue as all three characters learn something about their individual desires.

With a focus on a complicated female friendship and a well-observed critique of how much time overeducated Torontonians supposedly "working on their grant" can spend dwelling myopically on sex and dating, Miss Misery has some of the funniest and most perceptive dialogue in all of Canadian media. It's a painful, miserable, heart-rending delight.

To be in a good relationship, you have to be amazing at communication, you have to be self-aware, and you have to be secure in talking through the difficult things. To be an open relationship, you have to be all that and more.- Jade Blair

Largely funded through a $20,000 Kickstarter campaign, the show is stylishly shot by cinematographer Luke McCutcheon with an engaging cast of charismatic newcomers (Waterman, Thomas, and Blair are all first-time performers). There's also a star-making performance in Waterman's childlike, searching Amy. She grounds the series with her own empathetic desire for sexual gratification while not wanting to hurt her longtime partner, who all too readily agrees to an open relationship.

The show satirizes the existential hellscape of dating in Toronto, a city whose growing financial instabilities turn every casual date into a stressful job interview, while hinting at a possibly true stereotype that couples can use ethical non-monogamy as a way to prolong an inevitable breakup. Using Amy, Jay and Lee as our own broken avatars, Miss Misery explores the sexy highs and uncertain lows of navigating casual sex and dating and does it without judgment.

"The point of the show is to watch people who are not ready and maybe not even orientated to being in non-monogamous relationships attempt it," Blair said over coffee in Toronto's Kensington Market neighbourhood. "To be in a good relationship, you have to be amazing at communication, you have to be self-aware, and you have to be secure in talking through the difficult things. To be an open relationship, you have to be all that and more. No one in this show is succeeding at closed, so all of a sudden it puts the video game on hard mode."

Co-creator Steve Thomas agrees. He thinks millennials engage in open relationships because a lot of the usual goalposts of adulthood (like owning a house, having kids, and getting married) just aren't as realistic anymore.

Miss Misery. (One Ten Productions)

"One thing that does make sense to me is that the milestones of generations past are either harder to get, or are seen as less desirable," Thomas said. "If you live in a big city and you're trying to create a new family around you, burrowing yourself into a hole with another person can make you feel cut off."

"Our baseline reference for the show was Girls. We talked a lot about how the form of our story centres on this one woman and her best friend and her boyfriend. Can these two relationships more or less be given equal screen time and what does that mean for the audience's sympathies? Is Jay actually the villain?"

In making their DIY web series, Waterman, Blair, and Thomas, alongside their collaborators Luke McCutcheon and producer/editor Alison MacMillan, took a collective approach. While the inception of the series began three years ago when Blair and Thomas were living as roommates, it soon broadened to incorporate everyone's personal experiences and feedback.

On set, Thomas and Blair would trade off on directing scenes, looking to all of the cast and crew for feedback. All three leads have first-hand experience with their subject matter and remain sympathetic to every character's perspective. Whether you're entering a new relationship while trying to honour the wishes of your partner, or are desperately single and hoping not to catch feelings, it's complex, emotional territory rife with dramatic storytelling potential, especially for three characters whose greatest fear is an honest conversation about their own expectations, wants, and needs in the pursuit of love. 

"I think Miss Misery is unique in that it blends humour and seriousness, and doesn't really have a didactic angle," Waterman said in an email. "It's not yelling about how being open is 'really good' or 'a disaster,' but rather exploring the nuanced interiors of what they can do to people's interpersonal and internal landscapes. They show how opening things up can make a person sexy and vital one minute, and then deeply vulnerable and neurotic the next."

"I think what is completely new for audiences really depends on the audience, but I think that older and more heteronormative audience members might be more surprised by the realism and accessibility of the content."

Said Blair, "Committing to someone is really scary, so I think a lot of folks make their boundaries permeable so they can feel less upset. The more we talked, trading 'war stories,' we realized we were all dating people who were in relationships with someone else, or watching our friends attempt to date people outside of their primary relationships. It was just everywhere, and everyone's like 'Oh, you've never had oat milk? You'd love it.'"

About the Author

Chandler Levack is an award-winning writer, journalist and filmmaker. In 2017, her short film We Forgot to Break Up premiered at the Toronto International Film Festival and SXSW. She is currently working on her first feature Anglophone.