Ozzie wants to celebrate his 30th birthday by asking his girlfriend Penny to marry him. This seems simple enough but, as Ozzie learns, nothing is simple when you are turning thirty. Ring box in hand, Ozzie embarks on an odyssey of unresolved issues that threaten his romantic plans. He must contend with his bumbling roommates, the return of his prodigal father, the devious schemes of his persistent ex-girlfriend, and Penny's devastating confession.

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