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After the devastating demise of a six-year relationship, Melissa flees New York for Cape Town to recuperate and plot her next move. The last time she was single was in her teens, and now a few days after her 40th birthday, she finds herself at a crossroads. Enter Emily, Melissa’s best friend, who flies halfway across the world to Cape Town, to offer Mel a shoulder to cry on. Emily’s dangerously close to exiting her 30s as well! Unlike Mel, Emily’s last real relationship is a phantom in her distant memory. Yet, as both women find themselves on the cusp of a new decade, they are figuring out the same things: relationships, careers, themselves …

However, when Emily arrives expecting to find Mel down in the dumps and licking her wounds, she’s greeted with the opposite. Mel’s looking light and happy and has already met a new man, Gerry – an aging British rock star who is trying to put his crumbled life back together after a series of bad luck and bad decisions. Gerry is sojourning in South Africa, courtesy of his best friend, Baz, a wealthy money-guy and bona fide modelizer. Sweet, funny and big-hearted, Gerry is a complete 180 from Mel’s ex-fiance?, who was also her boss, Javier – a sleek, successful and controlling businessman, who is currently running his Argentinian family’s wine business in New York. Mel was their top wine rep, an ace at her job. Javier’s last violent outburst was the last straw, and Mel finally left him for good. And now she’s homeless, jobless, and essentially penniless, since Javier promptly fired her and wiped out her savings account in a bold move to keep her under his thumb. Silkily handsome, Javier is still very much a presence in Mel’s life, via terrifying, threatening text messages and calls.

Gerry and Mel seem completely infatuated with each other…but will it last after Mel meets Willem, a local boy made good, who has the charm of Gerry, as well as wealth and success, and none of the bad decisions? Fresh off the boat, Emily soon finds herself immersed in the worlds of glitzy Cape Town and the luxe surrounding Winelands. The duo rolls with minor European Royalty, Trustafarians, artists and billionaires. Disillusion soon strikes Emily when she realizes that Mel has, in her usual form, abandoned her for the affections of yet another man – Emily is lonely, and furious at having to explore this foreign country on her own. Mel’s self-serving attempts at matchmaking, only add fuel to the fire. All this for a romance that is clearly doomed to failure, in her opinion – so much for girl time in the Winelands!

Then she encounters James, sweet, kind James, a handsome local scion, with a firm belief that he is destined to be a star in the music world. His constant pot smoking and seeming lack of drive doesn’t even bother her too much either. He seems to be enamored with Emily. But, he is definitely not the man from her vision board. Plus, what would her glamorous self-help guru say about all this drinking, meat eating and fraternizing with capitalists? Is this really the life she’s meant to be living?

Together Mel and Emily discover who they really are, and what really matters, as they figure out what direction they need to take with their lives, one sip at a time. Sideways meets Vicky Christina Barcelona with flavorings of 500 Days of Summer.