IMDb 6.8 2016 HD

Can’t Win. Do Try.

Can’t Win. Do Try.

2016
Comedy Drama
106 min NR Australia
4 / 10
6.8 IMDB

In a bid to extend his adolescence, Gordon convinces his reluctant fiancée to allow his best-friend Jez and himself to live in the house they have just bought…

Personnel // Cast & Crew

Director JJ De Ceglie
Starring
Adriane Daff / Fiannah de Rue / Matt Furlani / Chelsea Gibson / Cj Hampson / Tanya Jade / Christopher Millington / Aimee Claire Nicholls

How Viewers Describe This Film

Common themes and sentiments

relatable humorous awkward charming frustrating honest predictable light-hearted thoughtful immature endearing

Reviews

I
Isabelle Dubois
Apr 17, 2026
2.5 / 5
2.5

The premise of "Can't Win. Do Try." – a man attempting to extend his bachelor years by turning his marital home into a temporary pad with his best friend Jez – is a concept that could either soar…

J
Julian Finch
Apr 17, 2026
3.0 / 5
3.0

Director Unknown tackles the perennial theme of male reluctance to fully embrace adulthood in "Can't Win. Do Try.". The narrative follows Gordon's attempt to freeze time by establishing a bachelor pad with his friend Jez in the house…

P
Penelope Croft
Apr 17, 2026
4.0 / 5
4.0

"Can't Win. Do Try." presents a refreshingly honest, albeit potentially awkward, look at the anxieties surrounding commitment. Gordon's unconventional proposal to his fiancée – a year of bachelor pad living with his best mate Jez in their new…

M
Marcus Bellweather
Apr 17, 2026
2.0 / 5
2.0

The concept behind "Can't Win. Do Try." feels like a well-trodden path: the eternal bachelor refusing to grow up. Gordon's insistence on a year-long bachelor pad in his newly bought home before marriage, alongside his friend Jez, sets…

E
Eleanor Vance
Apr 17, 2026
3.5 / 5
3.5

In "Can't Win. Do Try.," director Unknown navigates the tricky territory of male arrested development with a premise that promises both humour and potential pathos. The story of Gordon, his best mate Jez, and a fiancée whose patience…

FAQs

The primary conflict stems from Gordon's desire to cling to his adolescent freedom by proposing a year-long bachelor pad scenario in his newly acquired home, much to his fiancée's likely chagrin. This creates immediate tension between Gordon's wishful thinking and the reality of his impending marriage and the compromises it entails. The dynamic between Gordon, his best mate Jez, and the fiancée will likely drive the narrative's conflicts.