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book cover for The Second Most Awkward Man in Spain

The Second Most Awkward Man in Spain

More Dispatches from a Philosopher Abroad

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Book 3 of Awkward Man

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Pub Date 7 Jan 2027 | Archive Date 10 Dec 2026


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Description

What if the secret to a good life is giving up on being the best?

Robert Gressis has a problem. He wants to be great: a great philosopher. A great writer. A great singer. A great traveler. Ideally, he'd also like strangers to recognize his greatness without his having to mention it.

Unfortunately, the evidence isn't cooperating.

So Gressis heads to Spain with his old friend Franklin, a successful philosophy professor who possesses something Gressis finds both enviable and suspect: the ability to decide that something is good enough and then move on with his life.

Together they eat their way through Barcelona, San Sebastián, Madrid, and Seville; encounter sublime churches, baffling museums, spectacular meals, disappointing spectacular meals, Spanish trains, social misunderstandings, and the occasional threat to human dignity. Along the way, Gressis wrestles with the questions that have plagued philosophers for centuries: What makes a life go well? Can lowering your expectations actually make your life better? And why are birds such assholes? 

Part travel memoir, part philosophical inquiry, and part extended demonstration of why some people should never be left alone with their own thoughts, The Second Most Awkward Man in Spain is a funny, self-lacerating exploration of ambition, friendship, mediocrity, and the exhausting pursuit of being exceptional.

Because maybe being second-best isn't a consolation prize. Maybe it's the point.

What if the secret to a good life is giving up on being the best?

Robert Gressis has a problem. He wants to be great: a great philosopher. A great writer. A great singer. A great traveler. Ideally...


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EDITION Ebook
ISBN 9077219251683
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PAGES 220

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