The Naked Wanderer (2019)

Cock-eyed optimist Jake (Angus McLaren) surprises his girlfriend Jasmine (Megan Smart) with the chance to swim with the dolphins and it’s in the middle of the ocean that he proposes to her. She turns him down, citing that she wants to be with someone who is all around “more” than Jake and that she’s unnerved by his constant happiness, which ironically, makes him very sad, and his sadness is compounded when he loses his job because her father is his boss. He and his roommate Cameron (Callan Durlik) come up with a plan for him to embark on a 2.5 thousand kilometer walk across Australia to win her back, and Cameron’s millionaire uncle Brian (John Cleese) agrees to sponsor this endeavor under one condition - Jake must be naked, with his only covering being a tiny loincloth. This obviously draws a lot of attention along the way, including from fellow traveler Valerie (Natasha Liu Bordizzo) who we see sunbathing on the beach in a string bikini. The two hit it off, but of course there’s still Jasmine, and it looks like Jake’s newfound fame might have changed her mind about him. It’s obvious which one we would choose!