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With only one other, rather unsettling film to his name, director JJ DeCeglie has created a genuinely hilarious film with Can’t Win. Do Try.
Can’t Win. Do Try. follows Gordon, an engaged 25 year old with a fresh mortgage. In a bid to extend his adolescence he convinces his reluctant fiancée to allow his best-friend Jez and himself to live in the house they have just bought in a bachelor pad situation for the year before they get married.
Jez organises a third housemate, O’Hara, who enters the house and adds his personal brand of crazy to their everyday existence.