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Leonardo DiCaprio's Teenage Hookup Detailed in New Memoir

Leonardo DiCaprio's Teenage Hookup Detailed in New Memoir

Leonardo DiCaprio takes a moment to bask in the heat of the sunlight while waiting for his car to arrive on Saturday (November 16) in New York City.

The 39-year-old actor allegedly had a one night stand with video vixen Bobbie Brown back when he was only nineteen, and now the hookup is being detailed in her new memoir “Dirty Rocker Boys: Love and Lust on the Sunset Strip.”

“I unbuttoned his jeans and tugged down on his boxers,” Bobbie, who was twenty-six at the time, wrote in the book (via The Daily Mail). “(What) I saw made me gasp. It made no sense. The kid put Tommy Lee to shame.”

“Waves of satisfaction rippled through my body. If only Tommy Lee could see me now. He was a unicorn. Rare, innocent, and horny. Me, on the other hand, I’d been engaged, married and had given birth. I needed a man, not a man-child,” she added.

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Photos: SplashNewsOnline
Posted to: Leonardo DiCaprio

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  • the truth

    Rose: “Id rather be his (LEO) wh*ore than your wife” haha every girl probally wants to say this to some loser….

  • Leo’s Fantasy Girl

    I had sex with Leo. (In my fantasies) Does that count?


  • Zzzzzz

    @also…: It was the daily mail online UK where she said …It was DiCaprio, however, with whom she nearly went all the way (she had been approached by Stephen Dorf and turned him down). She describes taking off his pants and he starts asking if she had been tested for diseases…. To me, if they had sex, why would she say she nearly went all the way? To me, having sex – is all the way! That doesn’t make sense – but the way the different gossip sites are picking and choosing what they print, it’s kind of confusing. I wouldn’t be surprised if he did. If Page 6 is correct at least he does use condoms and is concerned about stds.

  • ####


    So who’s going to read the book to confirm?? LOL

  • Zzzzzz

    @####: LOL! I wouldn’t waste my money! I think it’s sad when people do these tell all books. She is definitely using Leo’s name to sell the book. Not saying Leo hasn’t slept around, but I don’t know of a 19 guy that would have turned her down. She was so popular and all the guys were crazy about her.
    re Disneyland: that sucks! Are you going to re-schedule the trip?

  • Isa

    Love these pics ! He seems so peaceful in it !
    La parenthèse Enchanté

  • Nice

    OMG love these pics. i do that too when I’m in the sun, the direct sunlight on your closed eyes is very good for your eyes, plus Vit D like someone said. He looks better in casual clothes than when he wears a suit.

  • ####


    He was 19 and a horn dog so I gave no doubt the probably slept together but it’s weird there’s a discrepancy with these gossip rags! Wouldn’t they just have someone read the book to confirm it?

    Re Disneyland, we’ll probably plan the trip for the beginning of the new year

  • Zzzzzz

    @####: I don’t think the book has been released yet. I think she is promoting it before it goes on sale.
    re Disneyland: that’s probably a good time to go. It shouldn’t be too crowded!

  • ####


    But wouldn’t media outlets get an advanced copy before it was released? I don’t know how that works…..

  • Sighting

    Norm Clarke @Norm_Clarke 2h
    At #UFC 167 (MGM Grand): Arnold Schwarzenegger, Leonardo DiCaprio, Jeremy Piven, Shane Victorino, Ryan Howard, Larry Walker #MMA #vegas #FB

  • Zzzzzz

    @####: You would think… but maybe ti’s such a poorly written piece of crap that she is only giving tidbits to build a buzz…. Who knows, but just reading some of the excerpts, it doesn’t appear to be written very well.

  • Zzzzzz

    Typo * it’s. ..

  • Sighting

    Pic of Leo at the fight tonight in Vegas

    Lord Michael @GoldieMikeyx 4h
    Look at Leo at the ufc fights

  • Sighting
  • Sighting

    typo *Lukas’

  • LOL42

    Thanks for the sightings.
    I actually wished he was going to Austin. I guess the partying is really non stop for Leo at this stage *Sigh*

  • @64

    Thanks. Lol random? That wasn’t even a very big or important fight as far as I know but oh well.. Leo. He’s got luggage in these pics so maybe he’s stayin at the West Coast for a while.

  • Yup

    So, he played the good boyfriend for a little while and needed a getaway to Vegas afterwards with Lukas. Leo and Toni really are the weirdest couple ever.

  • @69

    She is not exceptional in any way tbh. This is how Leo always has been.

  • LOL42

    Exactly. I hope this does not turn into another ex-girlfriend discussion thread but this behaviour is very typical of Leo. Same old Same old

  • and…

    maybe she’s with him…?!

  • @71

    Seriously I sometimes think there are so many people who just started following him closely thus make such a big deal out of Leo behaviour that is so typical Leo. There are things that surprise me too but in general this is just how he is. 90% of what he does is so damn predictable.

  • ❤lovesick❤


  • also…

    If she is there a clue is on the way…

  • @2724-last threat

    @BZ – last threat

    My first language is german, I can not speak english very good. Someone on the last threat asked if anyone understand german to translate what Toni said. So I want this to translate. The anchorwoman asked Toni “Is your family here at show? Your mother, or your brother?” Toni said: ” No, nobody is here.” The anchorwoman asked: “And what about ? Is special one here?” Toni said: “No.” The anchorwoman said: ” You have a very famous boyfriend. How is it so? You have to hidden from paparazzi?” Toni said: “I don`t talk about private, nothing personally.” The anchorwoman: “Why? Because The Victoria`s Secret do not want this or you do not want to talk about personally?” Toni said: ” This here is a show and I don`t want to talk about personally life, we have here right now a show.”


    So I hope you can understand what I wrote what Toni and the anchorwoman said.

  • @2724-last threat

    *And what about special one?

  • @76

    Thanks for the effort!

  • newbie

    He looks cute in these photos lol

    Anyway, I meant to respond in that other thread but I got busy.


    One was in Australia when he was filming Gatsby. She’s a brunette and an inspiring model in her early 20s. They met at a club when he was drunk. They went back to her model apartment (it’s like a dorm almost) and had sex. She said the size was fine but he was lazy and sloppy because he was drunk. So she was disappointed with her encounter. I also have another friend of a friend in Australia who slept with him around the same time (I don’t know her personally I know the guy who knows her). She was upset that she was just a one night stand but didn’t give any details. I got the feeling that she was disappointed in general because she’d been a casual fan for a long time and him being lame in bed turned her off.

    Guess what, that Gatsby screening + after party is $1900+ to attend on the 25th and $2500 for December 17th. I love Leo but not that damn much lol

  • Sighting

    charlie sinclair ‏@TiffanySinclai 10h

  • well

    …He usually brings his blondies to Vegas when he attends boxing games.

  • Is DiCaprio into meditation?

  • HAHA12

    He looks good here, but I can’t believe he’s back to partying already. Where does he get all the energy?!

  • @76

    I do not believe she don’t want to talk about her relationship at all. She probably would love to. I think she meant to say she can’t talk, is not allowed to talk, is forbidden from talking etc… about Leo in interviews. There is a difference

  • Black sharpie
    I know this is old but the way the article is written is hilarious ! I love Dlisted. It’s all Cara’s fault. She turned him down and he went after Toni. Lol

  • Black sharpie

    I still think one of his exes is going to talk someday, non-disclosure agreement or not. My money is on Bar.

  • HAHA12

    @Black sharpie:
    Hasn’t she already technically? I remember seeing an interview posted a long time ago where she was talking about Leo and how she wasted a lot of her life to be with him or something. And Kristen Zang has talked about him too.

  • good job

    @@2724-last threat:

    Thank you! Your English is very good, btw. I understood everything. :)

  • luke’s clues

    Lukkas often drops “clues” about where he is, too. How come no one makes a fuss over them? I don’t care if Toni is in Vegas. Lukas is there.

  • ####


    Surprisingly he hasn’t taken her to vegas yet. He left her in LA after that Halloween party when he went to vegas the next day so who knows if she was there or not. It seemed like he was waiting with his friends to be picked up but they could have picked toni up on the way to the airport.

    In Lukas’ mobli video, I think the bald guy in front of him to the right is the president of the UFC Dana white and also in that pic with Leo?

  • ####


    Never mind. The pic and the vid look like the same guy but not Dana white.

  • Black sharpie

    I mean a more in-depth type of thing like a book or long interview. Something that will make money and/or get her lots of publicity.

  • Valentina
  • Valentina
  • Black sharpie

    The story about him trashing a hotel room was refuted by his people.

    I do agree he is very close to his mom, probably because he is an only child and his parents divorced when he was young. I wonder if the reason he set her up with her boyfriend was to try to separate himself from his mom a bit?

  • @92

    I can’t see Bar do that TBH. I bet she’d love to but that would possibly account for lots of trouble if she’s signed a non-disclosure. Leo could even sue her and I don’t think starting a war like that is what she’d want. It would gain her publicity and money but she would probably also lose a lot of money because of the non-disclosure. At this point I am positive Leo, his lawyers and his people are so powerful that they could destroy her.

  • Instagram

    Toni’s in her hometown in Germany. She just put up a pic on Instagram.

  • Black sharpie
    It’s amazing that this man hasn’t literally fallen flat on his face trying to avoid the paps!

  • ####


    AAWWW….Leo didn’t want to go with her to see the fam???

  • hm