How is Leonardo DiCaprio Not Bored With His Life Yet?

Surely it’s all getting a little old

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.

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  • Rachel D.

    MR is seriously READING MY MIND TODAY. Loved this soooo much! Also watched Titanic yesterday…

  • Kristen J

    Someone should try the Leo Diet to officially find out if this is boring or not.

    • Sonia

      I volunteer as tribute

    • First we need the $

      Charmaine Ng
      Architecture & Lifestyle Blog

    • Hayley

      Harling should do it.

  • KTD091

    eh, i think he’s just tired & sitting on yachts is all he’s got the energy for. I have close friends who work in film & the whole movie-making process (negotiations/development, shooting the thing, post work, press tour, awards season if you’re lucky) seems pretty exhausting. its even worse for actors who also produce, which idk if Leo does or not. he does have that charity!

  • Meighan Gerachis

    You are my MR star. Love yr writing. Imma say this– Cintra Wilson– read her

  • Patrizia Chiarenza

    One of the (many) reasons I believe Leo is my soulmate (and I’ve believed this since I was 12) is because if I had money, that is EXACTLY the kind of life I would want. On a yacht, by the beach, surrounded by a mix of my people and other interesting/good looking people, just livin’ life.

    He is doing it RIGHT!

    But please, someone do the Leo diet. There’s gotta be a boat you can use!

    • Re: Leo diet boat; the ferry?

    • Kiks

      Same. Can we be sister wives?

      • Patrizia Chiarenza

        haha yes!!

    • Inaat

      Haha, same! When I´m drunk always somehow end up telling people that Leo is my boyfriend and that all the other girls (edit: models) are just distractions for the paparazzi, you know- cuz I´m not about all that attention.

  • ValiantlyVarnished

    As an actor I think Leo is fantastic. As a real life person? I think he’s a bit of a douche. He is no different than every other successful rich guy in Hollywood. 40-something man who only dates blonde (MUCH younger) models who all look so similar one of them could commit a crime and every easily blame the other for it. Witnesses would not be able to distinguish them in a line up. He’s a modelizer (which carries with it an unmistakable whiff of misogyny). I DO think his life seems pretty boring. I never look at paparazzi pics of Leo and think, “Wow. that looks like an amazing time.” I always think (with eyes rolling back in my head), “Leo is hanging out on a yacht with ANOTHER blonde model and his “Boys” (“Boys”, who like Leo are actually grown ass men in their 40’s). Lame!”

    • Marisa Brenizer

      How does that make him a douche?

      • Laura Guarraci

        yea, having sex with a lot of really attractive people who are dying to do so doesn’t really make you a douche. it may make you a bit shallow, but maybe he saves his emotional depth for movies, the man is an artist! at least he doesn’t lie to women/marry them and cheat on them with reckless abandon- that’s a worse hollywood trope.

        • Laura Guarraci

          that said, i wouldn’t hate it if he threw a brunette in there once in a while.

          • I saw some photos and there’s a brunette among all the blondes 😉 sometimes he steps out of his comfort zone

          • ValiantlyVarnished

            He does. But then he hides it. He and Rihanna dated for a few months and he apparently didn’t want to go public with it so she basically became a glorified booty call meeting him in hotels. Rihanna! I would have had a thousand times more respect for him for dating a woman who was equally successful as he is. But nope- after they split he immediately went back to dating semi-successful 20 year-old models. Publicly.

          • Well, they often hang out together and the whole world knows that they have been dating, but I understand what you mean, they are friends with benefits, but if she’s ok with it…

        • ValiantlyVarnished

          Of course there are worse Hollywood tropes. That wasn’t my point or my argument. I think we tend to give famous men a pass for behaviors that if we saw them exhibited in people we actually know we’d take issue with. There is somthing skeavy about 40 year old men dating 22 year olds. Period.

          • Lil

            Exactly. If I had a friend who consistently and for years only dated people half their age, I’d reevaluate that friendship.

          • I agree with you. He’s a great actor, an environmentalist (even if sometimes he doesn’t act like he is) but he seems to be a bit shallow. I joke about all the models he dates saying he is “a talent scout” because let’s be honest, 20 years old girls perfectly know that dating him means becoming famous and many 20 years old girls would never go out with a man of his age if he wasn’t famous and rich

          • TF Beauty

            Well said!

      • ValiantlyVarnished

        Seriously? You dont think a 40 plus year old man who only dates 20 something blond models for about 6 mos – tops- isn’t quite possibly- a giant douche?? At the very least he’s a giant man child. And giant man children tend to be douches.

        • Marisa Brenizer

          I don’t, actually. Still not seeing the correlation, tbh! I don’t vibe with generalizations or assumptions based on superficial evidence.

          • ValiantlyVarnished

            Like I said in my original comment, there is something slightly misogynistic about a man who only dates women half his age and of a certain specific look and type as if they are vaguely interchangeable. That’s the vibe I get from Leo. You can call that an assumption or a generalization if you like.

          • Quynh Tran

            Why is he so stuck in that age group of 20 something women??? Seems to me that women get more interesting once they hit 30. Plus, he doesn’t predominantly hang out with 20 something guys. What a douche…

          • missmg

            Also he dumps them just shy of their 25th birthday its like he is allergic to women older than 25 let alone anywhere near his own age. He is gross.

          • ValiantlyVarnished

            Exactly. Thank you for getting my point

        • Lisa Barbaria

          Most men are just giant children…

        • Sq

          Yep it’s creepy and weird.. he stopped dating people his own age in the 90s!

  • Jessie Buckmaster

    I’m amazed he still has time to be on yachts with all the saving the environment and being UN ambassador and such. His commitment to climate change is what truly made me fall in love (sorry baby Leo).

  • Sarah

    you did seem to forget about a large portion of what leo spends his time doing.
    equal parts Captain Planet and I’m On A Boat…. I would take his life any day!

    hilarious story as usual!

    • TF Beauty

      You actually don’t know what his life is really all about. You see all of the great parts but you actually have no idea what goes on behind closed doors. Never long for someone else’s life.

  • I was literally just musing this on Sunday. I don’t know what being bored of LDC’s yacht lyfe makes me but I’m glad I’m not alone / we’re finally having serious discussions about it.

  • Jennifer

    Ha! Let Leo be! He’s been working since he was a kid, has made (acted and/or produced) some of the best films in our life time, and has a genuine interest in environmental issues that he’s active in! Let the man strut around the South of France with 22 year old blondes on his downtime. Lord knows, if I had the means, I too would round up all my friends, go out on a yacht and have a fun summer in France! I don’t care if I’m 80 years old, I don’t think it can ever get old.

  • Lindsay D

    great article Haley- try the diet

    I often wonder if he would like my company. Just this weekend I wore a dad hat and sunnies and lied on the beach SOUL MATES

  • mary-paula allegaert

    Hilarious piece. Leo, not so much.

  • Vida Rose

    Best use of the phrase ‘chicken or egg situation’.

  • xtyb
  • Min Zee

    My curiosity got the best of me but finished reading this boring story anyway -hoping for some sort of illumination -wishful thinking-don’t know why I even considered such a thing

  • missmg

    Great story Haley. Cannot believe people still like him. Also he is an advocate for the environment yet flies private jets constantly. He is a full blown man child and there is something really douchey about hanging around with “the boys” and exclusively dating 20 year old models well into your 40s.

  • allison fargo

    is leo only fighting climate change so he still has a good-looking ocean to cruise on? the world will never know.

    • Olivia

      The accuracy of this statement … bravo.

  • Emmie

    the life size cut out of him that i have in my room begs to differ that lying on yachts is *~all he does~*

  • Theory: he doesn’t do it for fun, it’s just his life. Hear me out (this is not a diss of this article, I love weird thought provoking stuff like this).
    As you said, he is a megastar. As such, perhaps his life has transcended any kind of normalcy to the point where this is his default, not ‘fun’, just normal. Like, no one asks me ‘god, you brush your teeth twice every day, you must really love it’ because it’s just standard routine. Hanging out with models = teeth brushing when you are Leo. It’s not fun, not unfun, just neutral, autopilot life stuff that you do while checking your phone. That’s my theory anyway.

  • I love DiCaprio since… forever. He’s my favorite actor and I find him one of the most attractive men on Earth. I admire him for his commitment to our planet and so on, that’s why I can overlook the fact that during his vacations, he basically does the same things he did 20 years ago. He plays with his friends like they were still kids (with water guns!!) he dates girls that could be his daughters, he bores himself on super expensive yachts. And many men envy him (because of all those models who surround him).
    I guess it’s just another typical summer for him, so why should he look excited?

  • Martha Pietruszewski

    But why Tobey Maguire

  • The Fluffy Owl

    If there are no photos of him using the toilet does it mean he doesn’t?

  • Emma

    the headline, is so funny, and i’ve been wondering that as well!

  • To each his own, actually.
    Maybe he has been seen in numerous of these parties, but maybe it’s just a way to do friends gathering for rich people, like, when we ask our friends to come over to our house, he asked his friends to go over to his yatch. Nothing special, honestly!

  • Larry david

    I am bored silly with this a-hole’s life

  • kaitlyn conway

    That yacht party honestly does look boring as fuck. But i bet for a few of those models it was their FIRST Leo Yacht party with The Boys™ making it the BEST day of their life which makes it even more sad ugh!!!!

  • Hansika Vijayaraghavan

    Maybe he never got over Titanic and sitting on yachts is his coping mechanism

  • Caroline Kloster

    “The Boys™” actually has me in tears

  • Ciccollina

    I agree, and the same-looking model girlfriends feel misogynistic to me. I have always had an aversion to men who have a “type” though, as if women have nothing more to offer than their visage.

  • Jordan


  • Someguy

    I wonder if the intent of the writer is to get clickbate or stir-up the readers. Leonardo has built a business, working with companies to educate those on illegal dumping, engaged with the President and generated over 80+ million dollars to protect land, animals, and the enviroment. Those yachts maybe boring as fuck to you.. but how much has the writer, other than shame an actor that is enjoying the fruits of his labor has done to equal even 1 percent of giving back to the community that Leo has done.

  • Kara Zawacki

    Ah, one of life’s toughest questions… No but really, this was a lot of fun to read (and The Boys™ was my favorite part). But also don’t forget he made that one doc on climate change!

  • Tess

    I’ve always hopped Leo would have a real life rom-com-esque transformation, where he finally meets a woman his own age (a sandra bullock type character) and realizes she’s the shit, and that’s what was missing from his life.

  • Rylee Nelsen he must’ve seen this and taken it to heart. I saw him this morning at 8:30 am biking on the west side parkway. he was with a model and seemed to be pointing out things to her, so he was probably doing it to impress her, but I was impressed he was out of bed and doing something active that early