Why Every Lesbian Needs to Watch Portrait of a Serial Monogamist (2015)

If you’re a lesbian who has ever jumped from one intense relationship straight into the next without catching your breath, congrats – you might just be the target audience for Portrait of a Serial Monogamist (2015). This little Canadian indie gem flew way under the radar when it came out, but almost ten years later it’s still one of the realest, funniest, and oddly comforting lesbian movies I’ve ever seen.

The story follows Elsie (played by the ridiculously charming Diane Flacks, who also co-wrote it), a 39-year-old lesbian in Toronto who has literally never been single for more than five weeks since she was 17. Sound familiar? Elsie is the queen of serial monogamy – she falls hard, moves in fast, plans the future after date three, and when it inevitably crashes, she’s already swiping on whatever the 2015 version of Lex was before the breakup tears are even dry.

The movie kicks off with Elsie dumping her sweet, stable girlfriend of five years, Robyn (Vanessa Bayer – yes, the SNL Vanessa Bayer, and she’s perfect). Everyone thinks Elsie is insane for leaving someone so great, but Elsie is already chasing the spark with a hot 26-year-old photographer named Lola. What follows is 90 minutes of pure lesbian chaos: awkward U-Hauls, exes popping up at parties, trying to “just be friends” while clearly still in love, and that excruciating moment when you realize maybe the problem isn’t them… it’s you.

Here’s why, as a lesbian, this movie hit me right in the chest:

It calls out our community’s serial monogamy culture without being mean

Let’s be honest – half of us have a dating history that looks like a game of relationship hopscotch. The film never shames Elsie for it; instead it treats it like the very specific lesbian pattern that it is. We fall fast, we merge lives, we get matching tattoos on month four, and then we panic when the honeymoon phase ends.

The cringe is REAL

There’s a scene where Elsie tries to stay friends with Robyn and ends up drunk-crying in her ex’s kitchen at 2 a.m. – we’ve all been there. Or when she’s dating the much younger Lola and realizes she’s become the “old lesbian with opinions about craft beer.” Painful. Accurate. Hilarious.

It’s one of the few lesbian movies that isn’t about coming out or tragedy

No one dies. No one gets hate-crimed. Nobody’s parents disown them. It’s just regular messy queer life in the city – dating, breaking up, trying therapy, dating your therapist’s friend (don’t do that). In a sea of tragic lesbian stories, this one feels like a warm hug.

The side characters are gold

Elsie’s best friends are the kind of brutally honest dykes we all need in our lives. They stage interventions, they drag her to bad lesbian dance nights, they call her out when she’s being a walking red flag. Also, shout-out to the cameo-filled Toronto lesbian scene – it’s basically a time capsule of 2015 dyke fashion (flannel, undercut, thick-rimmed glasses – iconic).

It actually has a happy-ish ending

Without spoiling too much, Elsie does some growing up. She learns (kind of) how to be alone. She figures out that being single doesn’t mean you’ve failed at being gay. And yeah, there’s new romance, but it feels earned instead of rushed.

Look, Portrait of a Serial Monogamist isn’t perfect. The budget is clearly tiny, some of the acting is a little theater-kid energy, and it’s very, very Toronto (if you’ve never been to a potluck in the Church-Wellesley Village, some jokes will fly over your head). But for a lesbian in her 30s or 40s who has lived through at least three “we’re basically married” relationships that lasted exactly 18 months each, this movie feels like free therapy.

Stream it wherever you can find it (it’s on Tubi sometimes, or just sail the seas – we’ve all done it). Grab some wine, text your ex “this made me think of you” as a joke (don’t actually do that), and settle in for the most relatable lesbian rom-com you probably slept on.

And if you watch it and suddenly feel personally attacked… welcome to the club, serial monogamist. You’re not alone.

(Now someone please remake this with today’s cast – I need a Gen Z version with TikTok sounds and everything.)