Will Leonardo DiCaprio ever follow in George Clooney’s wedded footsteps?

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As we’ve been so focused on The Last Great Bachelor’s wedding for the past week, I thought we’d take a moment to look at these photos of Leonardo DiCaprio, the other “last great bachelor of Hollywood.” Leo is actually more bachelor-y than George Clooney ever was, because George had an early marriage that failed and that was what put him off of marriage for so long. What’s Leo’s excuse? He’s never been married. He has been in a couple of big live-in relationships, with Gisele Bundchen and…? I don’t know, did Bar live him? Did Erin Heatherton? Does Toni Garrn live with him? God knows.

Anyway, Leo was out with his bros yesterday in West Hollywood. He’s still doing that ratty beard and long hair thing. Some people say it’s because he’s going to be playing some outdoorsman in the 19th century in The Revenant. Personally, I think Leo just really lets himself go when he’s not working. He didn’t work all summer. He just ate, drank, partied on yachts and slept with a lot of ladies.

So, will Leo ever follow in George Clooney’s footsteps? Will Leo find The One when he’s in his late 40s or early 50s? Will Leo need to “rebrand” himself as a man who can be with a woman of substance after decades of bingeing on models in their early 20s? Will Leo decide – like George – that he’s tired of his personal life being everyone else’s punchline?

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Photos courtesy of Fame/Flynet.

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67 Responses to “Will Leonardo DiCaprio ever follow in George Clooney’s wedded footsteps?”

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  1. Liz says:

    Is it me or does the beard make his features look even smaller? It’s really not working for him.

    • Jaderu says:

      It will be gone once he’s finished filming his outdoorsy movie. He’s already scratching and picking it like a family of hoarding squirrels have moved into it.

      • Aussie girl says:

        Yes he seems to be picking out his lunch from there

      • Intro Outro says:

        Nah, maybe he’s consciously using his beard to stash away bits of lunch and pick them out and munch on them when he’s hungry again?

  2. bammer says:

    I hope not. Nobody should be made to think they have to get married. It’s not the be all end all, only road to happiness.

  3. kri says:

    I am embrassed for him, at this point. If I rolled around town at my age, collecting men, not working, and heading up The Dong Posse it would be sooooooo sad. (Wait, no that sounds awesome.) But seriously, can a woman get away with this stuff? Cause I gotta select some possibles for my Dong Posse.Off to work.

  4. perplexed says:

    He may marry later in life, but I think he’ll be more private about it.

  5. Jegede says:

    There are many Hollwyood bachelors Leo’s age and older.
    John Stamos, Joaquin Phoenix, Jamie Foxx, Adrien Brody, Gerard Butler e.t.c

    And of course the many HW stars who are married but still live like bachelors.
    *wink wink*

    Best be like Derek Jeter IMO.
    Stay single and hound; rather than Tiger Woods of get married and keep hounding

    • Kiddo says:

      Didn’t Derek Jeter just say he wanted a family after retirement?

    • magpie says:

      JP and GB fall into the same category but Stamos was married to Rebecca R and Adrien had a long thing with Elsa what’s her face.

    • Someonestolemyname says:

      Leo is in his thirties, he’s hardly some old approaching 60 bachelor who voiced constantly he hates being married and he’s a bad husband, like George.

      I see the two men as completely different.
      I don’t think Leo is hiding behind anything, I think he’s just being a single man who likes women.

  6. Jackson says:

    I could not even imagine dating someone with such a deep bro attachment as Leo seems to have with his ‘posse.’ Friends, close friends? Sure. But his group is just so damn skeevy and they appear to always be attached at the hip. I imagine some day he will get married though – probably around 50 years of age…..to a 20-something, former model….and soul-mate, lol.

  7. Jaderu says:

    3 Dicaprio truths ( In my head anyway )
    1. Leo will always have his boyish good looks
    2. Leo will never beg for an Oscar
    3. Leo will never get married

    *sigh*
    I suck at prognosticating.

  8. Luca26 says:

    Nah he’s a much worse case than George. He’s permanently stuck in adolescence . I think he’s going to follow the footsteps of Jack Nicholson maybe a few kids and longterm main chicks who tolerate side chicks but no marriage.

    • Someonestolemyname says:

      Difference is George has beards, whereas Leo has women he dates and enjoys but is not ready to marry.
      I think Leo is younger and more honest than Clooney.
      Leo just seems like a guy in his 30s, approaching 40 who enjoys woman and makes no bones about it.
      Whereas George made a big PR production out of every girlfriend and constantly complained about marriage.

      There’s nothing wrong with men or women staying single and dating if that’s what they choose and they are honest about it.

      • moot says:

        Projecting much? What do you really know or think you know about either man?

        Leo got famous much younger than George. Huge difference number 1.
        George has been married and divorced, and rather scarred by it. Huge difference number 2.

        Neither man has any high ground to stand on concerning their relationships in the past two decades. This is a choice between sh*t and diarrhoea. But from where I sit in the cheap seats, I would venture to guess that the women who dated Clooney got treated far better than the women who dated DiCaprio. If I had to choose, I’d choose George, because at least if he was choosing me back, I’d know that he was going to be a gentleman about it when it was time to end it. With Leo, I’d expect a text message to come clear out my stuff while he was off to Miami with his posse for the weekend.

        Not saying Clooney isn’t a cheater but at least he’d be kinder about it (and there’s probably be some clause in the contract about that). Leo would just be a little entitled douchebag bro. Yuck.

      • Someonestolemyname says:

        George has BEARDS. IMO.
        Just my opinion.

  9. Talie says:

    No joke, he’d perfect with Paris Hilton — both overgrown children who never want to accept their age and will keep the party going as long as they can.

  10. Loopy says:

    If Cowell(fatherhood) and Clooney(marriage) managed I think anything is possible.

  11. pretty says:

    he is not good looking, attractive anymore. he’s aging horribly. look at Matt Damon. his face hasn’t really changed much compared to when he was in his 20’s, 30’s but Leonardo DiCaprio’s face has changed soooo much. soooo bloated. so not attractive. he was still, somewhat attractive in the movie The Departed but now like ew..

  12. Jac says:

    I can picture the wedding yacht cruising down those Venetian canals now…

  13. FingerBinger says:

    Leo will probably get married if or when he wants to have children.

  14. Hannah says:

    I couldn’t care less. Good actor but his private life is so predictable and boring.

  15. MollyB says:

    Clooney was always a serial monogamist. He always had some D-list girlfriend that he would keep for 12-18 months before trading her in for another one. You didn’t really hear of him tom catting around or cheating on his D-listers. Leo, on the other hand, does what and whom ever he wants. I don’t see him settling down.

    • Someonestolemyname says:

      I think Leo is more like a young Warren Beatty or Jack Nicholson, dating whomever he wants and really enjoys women, they aren’t BEARDs like Clooney’s fake romances.

      • JenniferJustice says:

        Re Leo – I think they are beards. There are a lot of blinds about him. Maybe not completely true or all true, but usually where there is smoke, there is fire.

  16. Beatrice says:

    I know several big-time hounds who professed to be permanent bachelors and they got married in their 50’s. My theory is these guys run out of gas at some point and realize they want someone to look after them as they age, not be chasing strange when they’re 60+. (Of course, they could want both)

  17. AryaMartell says:

    The simple answer is no. I think Leo is way more full of himself than George ever was. I’ve always gotten Marlon Brando vibes from Leo but I think he’s smart enough to not want to screw up the lives of any potential kids the way Marlon Brando did with his hedonism.

  18. HBIC says:

    For all we know, he might be having trouble finding someone who doesn’t only want him for his money or his fame.

    With that said… running around banging a bunch of anorexic models and hanging out drinking at bars and music festivals like a 25 year old isn’t going to have the smart, respectable ladies flocking to date you, either.

    Perhaps he’ll find someone one day… we’ll see.

  19. Blythe says:

    What is Leonardo’s type (other than blonde, white models)? I don’t see him being married to an Amal-type woman, nor a Kate Winslet or another Bar/Erin.

    • Someonestolemyname says:

      But why does he need to marry ever and why does he need to change his type of woman, it’s what he likes.
      He can do as he pleases, he doesn’t seem to be hiding anything.

  20. magpie says:

    Didn’t Lainey say he and Toni were dunzo?

  21. Eleonor says:

    If one day Leonardo di Caprio will go full bridezille like George Clooney that will be one of the signs of the Apocalypse.

  22. Someonestolemyname says:

    I think the difference is George hired Beards and is not authentic in his personal life, but Leo is. He is a single guy who dates women/models for real, enjoys them, moves on to the next and he’s honest about who he is, it’s not fake. He likes models, he dates them and moves on to the next. Nothing wrong with that because he’s honest and not hiding behind them to cover something.

    The problem with Clooney is his relationships seemed Fake and like Beards to cover the truth of what he’s really about.

    • JenniferJustice says:

      I beg to differ. I think he’s closeted or Bi. The models are a front. Don’t find him honest at all.

    • moot says:

      And this is why gossip is a buffet. I don’t read that way about either man.

      To me George has been upfront (maybe not to the public, but moreso for his companions). Actually, even with the media, he’s always said his first marriage made him shy to do it again, and children just didn’t fit in with his lifestyle.

      ASAIR, Leo has never really allowed questions about his personal life or whether he was going to get married and have babies or not. His actions speak loud enough: he’s still in a teenage phase of hitting up the hottest babe in the room. And as long as he gets to do that, why would he buy the cow when he keeps getting fresh milk for free everywhere he goes?

      I see George as having been badly scarred by his first marriage — so badly that it made him repellent to the idea of marriage…until Amal. But since he’s already done that, fell in love before, there’s no reason to think he’d be incapable of doing it again.

      Leo? Doubt he’d ever been in love and doubt even more that he even wants to be.

      Not hiding behind anything with his behaviour? Um. Yes he is. Because sleeping with increasingly younger and younger models is very much hiding and not facing anything real.

  23. JenniferJustice says:

    When it comes to Leo, I always think of Lainey’s words, “Imagine this on top of you.” Please….no.

  24. word says:

    Not everyone has to get married. Also, let’s not assume all models are airheads with no substance, that’s not true. I am sure there are some models out there who are smart and witty and have good personalities. Being thin, tall, and beautiful doesn’t mean you’re lacking in other departments.

  25. Pumpkin Pie says:

    I like him as an actor but don’t find him physically attractive, not one bit.

  26. JoJo says:

    Don’t care. He’s rich, likes to party and doesn’t want to get married. Wow – sounds like a horrible person!

    • Someonestolemyname says:

      +1

      Single guy, with loads of money dates lots of gorgeous models
      That doesn’t sound like a crime at all, sounds like a young man doing as he pleases.

      I don’t get why some women who read about him need him married off. I’ll bet the men who read about Leo don’t care if he’s married or not.

      There’s loads of people who never marry. I saw a actress on tv in her late 40’s or maybe 50, tell a panel of hosts, she was never going to marry or have children and several of the women went completely ballistic on her, bombarding her with questions about her mental state, until one finally told them to back off of the actress. It was insane to watch.

  27. JoJo says:

    Don’t care. He’s rich, likes to party and doesn’t want to get married. Wow – what a horrible person!

  28. JoJo says:

    Sorry – something happened to my connection while posting. Didn’t mean to post twice!

  29. Annemarie says:

    The better question is will people stop caring whether or not Leonardo Dicaprio will get married or not? Maybe he’ll get married in the future, maybe he won’t. Why should it matter to anyone? His marital status has no effect on my life whatsoever. I don’t know why people are still romanticizing marriage these days. Marriage is not for everyone. If more people realized that, the divorce rates would go down.