How is Leonardo DiCaprio Not Bored With His Life Yet?

Photo by WireImage

Over the weekend, “news broke” that Leonardo DiCaprio spent last Thursday on a yacht with Tobey Maguire, The Boys™ and a cornucopia of models. For the special event, DiCaprio donned his best khaki shorts, Dodgers hat and Vans-esque slip-ons. Around his neck was a delicate gold chain, which he demurely tucked into his paper-thin polo. He looked, to put it most simply, exactly like Leonardo DiCaprio.

As I executed the important work of combing through the paparazzi photos, I noted the day appeared to pass, for him, not so differently from one I might spend on my couch: slouching, texting, biting my nails, staring at stuff. I had to admit that, when executed by Leonardo DiCaprio on a yacht, such activities enjoyed a certain sheen and appeal. I began to wonder: Do I think it’s fun to just sit there because Leonardo DiCaprio does it on yachts, or does Leonardo DiCaprio do it on yachts because it’s fun? It was a classic chicken or egg situation.

Photo by Empowers Media/Star Max/GC Images via Getty Images

I soon shook myself of such delusions. This yacht party looked boring as fuck, which begged an equally existential question: How the hell is Leonardo DiCaprio not bored yet? According to my long history of celebrity news consumption and continued surprise, Leonardo’s free-time is more one-note than a fog horn. For the last two decades, I’m pretty sure all he’s done between movies is wear baggy shorts and T-shirts in beach and beach-adjacent environments. Leonardo is always tan. He always wears a hat and sunglasses — never neither, never one, always both. His facial hair is consistently Tom-Hanks-one-to-two-hours-into-Castaway and he’s never not on the phone, with The Boys™ or in a budding romance with someone who probably had a 4 a.m. call time.

Taken day by day, it like sounds a real coup — a dream! — but as a collective description of his entire life since TitanicI’m left wanting. Doesn’t it ever get old? Does he ever take his pals on a jaunty hike? Go berry-picking with his family? How about skiing? Does he ever make snow angels? Christmas shop with an old friend? Play frisbee in the park with his dog? Or does partying on boats, walking briskly down boardwalks and staring off balconies always feel like the first time when done in the presence of high cheekbones and rich friends?

Because he’s a megastar — the likes of which only come along rarely — his life inspires many questions within me, but the ones I need him to answer most urgently are these: Could it really still be so fun? Could yachts, models and long-lens walks on the beach possibly hold the same luster after all this time? What else do you enjoy, Leonardo? Surely The Boys™ are busy sometimes.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

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