Lindsay Lohan and Leonardo DiCaprio are dating

January 10th, 2006 // 37 Comments

lohan-dicaprio-date.jpg19-year old Lindsay Lohan and 32-year old Leonardo DiCaprio are supposedly dating. They were first spotted kissing during Lindsay’s New Year’s Eve party at Miami’s Prive nightclub; and after she had her asthma attack, Leonardo allegedly visited her at the hospital.

A source told Britain’s Daily Star Sunday newspaper: “Leo visited every night. He would sneak in through a back entrance wearing a cap which covered his face. The 32-year-old actor is reportedly so smitten with the 19-year-old that he plans to fly to New York with her to meet her mother and manager, Dina.

I really hope this is true. Not because they’d make a cute couple, but because it’d be funny if Leonardo constantly made snide comments comparing Lindsay Lohan to Gisele Bundchen. “Oh, you’re eating dinner? Gisele never used to eat dinner.” And then Lindsay would run sobbing to the bathroom, two fingers down her throat and a bottle of laxatives in her hand.

Lindsay Lohan dating DiCaprio [Female First]


  1. candicec

    you’ve gotta be kidding me….

  2. Raider


  3. Lynette Carrington

    Oh, this is all kinds of WRONG!!!!

  4. Pesky Humans

    Leo clearly likes ‘em stable.

    *golfclap for the author on this article. Very funny.

  5. Tania

    Well he’s overrated, she’s definitely overrated…it’s a perfect match, really.

  6. It’s kind of like it’s a status symbol to have dated Lindsey Lohan or something. Everybody wants to do it for at least a day. Who’s up next?

  7. Beredon

    So… Leonardo DiCaprio is the father?

  8. sarakai

    OMG, she just cant stop! She’s the new ‘Typhoid Mary’ but this time its ‘Chlamydia Lindsay’ Somebody please sew her up and quick, before the baby pops out… I couldn’t stand another Lindsay out there! It’d be too many badly remade films to handle. Seriously, has she ever made a movie that was already a film? Parent trap, freaky friday, herbie- ok thats only three but three strikes and your out.

  9. aims_25

    Clearly she’s not as picky as Mischa Barton who said gross at the idea of being with Leo cos he was old.

  10. AmberDextrose

    Thank you Sarakai, that’s another mouthful of tea swallowed the wrong way this morning – the Superfiical comments are definitely getting back on form.

  11. Edie

    Wow. I wonder what she’ll be like when she’s old enough to drink LEGALLY!!!

    Nice cradle robbing their, Leo. I’m sure you two are intellectual soulmates.

  12. Roni

    Good God, did he suffer a head injury recently? What is he thinking? He can do better then that, doesn’t he have better taste? EWWWWWWWWW!! Shivers!!

  13. Leonardo DiCaprio has had a good life. He is going to ruin it behind closed doors with a 19 year old.

    “He would sneak in through a back entrance wearing a cap which covered his face.”

    Isn’t that how most old man pervs start out?

  14. parisdepaul

    Sorry guys to break it to you, but it is NOT TRUE. The reason being “They were first spotted kissing during Lindsay’s New Year’s Eve party at Miami’s Prive nightclub” so therefore Leo has already met Dina, Lilo’s Mom, because she was with her in Miami and wouldn’t have had to “fly to New York with her to meet her mother and manager, Dina”

  15. PapaHotNuts

    We’ve all seen Hagler vs. Hearns, Ali vs. Frazier, Tyson vs. Lewis, but how ’bout a catfight between Dicaprio vs. Valderrama? I can just imagine these two miniature sized boys bitchslapping each other outside of a Starbucks for the love of a bulemic, drug addicted, possibly pregant, definitely whorish, asthma-stricken, talentless chick. We’ll get Nick Lachey to ref the fight, and have K-Fed as a cut man and Stavros, Cisco, and newly single Chad Lowe as judges. Could be the fight of the century, or at least this afternoon.

  16. JerseyGirl

    Who isn’t she dating? Whore.

  17. Does this mean that you all would be opposed to me dating Lindsay then? I am 34, poor, not famous, and live in a crap-town in Northern Alberta.

  18. BrockSky

    Does this mean you all would be opposed to me dating Lindsay then? I am 34, poor, not famous and live way up north in Alberta… perfect for her, no?

  19. andrewthezeppo

    Why would he be “flying to meet her mother” if they met “at a new years eve party” every reliable source indicated that Lindsay was hosting that party and her mother was there. So she’s there and meets him, doesn’t introduce him to her mother then later he flies from somewhere for the introduction? That makes about as much sense as dumping Gisele so it’s probably true.

  20. ~S.Starr~

    “I want hotdogs Gilbert…I want hotdogs”

  21. parisdepaul

    ” So she’s there and meets him, doesn’t introduce him to her mother then later he flies from somewhere for the introduction?”

    … and also the fact that if he came over to the hospital every night, I bet Dina and Leo would have already been talking about when he first kissed a girl. This story is so fake!

  22. firecat

    Leo,”I’m having a birthday party (Lindsey), and your not invited, but you’ll cum anyway.”

  23. MortyFishbein

    Okay people, this confirms what I was trying to sear into your consciousness earlier: agents and managers are fucking pimps. And in Hollywood, the next hottest (or youngest) piece of snatch down the pike needs to make it around town in some way and the behind-the-scenes machinations of these people help facilitate that.

    Gisele was getting too old and too mouthy and learnbing new words like “self-esteem” and “self-worth.”

    That’s why Mischa Barton happened to be in the same room as Leo with the madame, er, agent pushing her over there onto him.

  24. WaitWhat?

    My lunch is starting to come back up

  25. HughJorganthethird

    Leo has always seemed a litle on the small and feminine side to me. I mean really what can this guy really be packing, 3, 4 inches tops? Im sure Lindsay will get tired of the artificial penis extender Leo must strap on every time they have sex, much like Giselle did.

    “Just hold on a minute Linda, I mean Lindsay,I can’t seem to get this one buckle done up…”

    King of the world my ass.

  26. nikki

    screwing a starlet and dating her are two entirely different things.

    i see that Lindsay is going the Maniston route — date a big star and you might start believing you are one. ha ha.

  27. PhDiva

    I live in L.A., and for years I have been told that Leo is gay, that he wanted to come out and his management wouldn’t let him. When he was with Gisele, I thought maybe I’d heard wrong. This Lohan thing convinces me that he really may be in the closet.

  28. HollyJ

    They’re both publicity whores.

  29. OMG!

    Does she really dig 32 year old gay men?

  30. ~S.Starr~

    Or maybe…just maybe…they actually like eachother.

    I mean look at Demi and Ashton…everyone thought Ashton was doing a bit for Punk’d. And now they are married. And look at Justin and Cameron…no one believed that and they have been together forover 2 years now.

    Ya never know….

  31. aims_25

    PhDiva: It also convinces me he is blind. From Gisele to Lindsay Lohan. What IS he thinking? Or perhaps should I say what is he thinking WITH? He figured he’d get more if he was with a whore like Lindsay perhaps?

  32. Seamus Begonia Smell

    so kate moss catches all kinds of shit for dating a 20 year old, and the only thing this 32 and 19 year old pair-up gets is a weight joke? come on superficial. there is something wrong with leo. and lindsay isn’t that pretty, i really don’t get the fascination with her!

  33. baileyukelele

    It’s going to be Strom Thurmand and Raven-Symone next.
    He’s dead? Even better.

  34. great job leo…way to totally sell yourself short

  35. dannyboy1

    Well, let me tell you all.

    I was searching a fileshare program and i had searched for leo on the program. What cam up was shocking to say the least; saw it with my own eyes! a video clip of about 2-3 minutes in length of leo in a bath tub being urinated on by two other guys. the closeup was real enough! The guy is a perv, period!

  36. anonymous

    Oh, no. No way. I have no or very little respect left for Lindsay Lohan. Seriously. Feel sorry for Leo, if he’s sinking that low. Didn’t he use to date normal, non-drunk-partying-on-drugs-all-the-time supermodels? Or unleast normal people? Not drugged little partygirls.


  37. Chiquita_Sexton

    It’s time we realize that most of these celebrity ‘hook ups” are fabrications orchestrated by the publicists. Face the facts, most male actors (and quite a few actresses) are GAY and the agents know that the public is just not able to accept the credibility of the performances in romantic/action films, so they pair the stars together and create phony love stories to litter the gossip columns and media stories. The movie going masses just love the idea of 2 stars ‘meeting on the set” and falling in love. Tom Cruise, for example is very gay, but has frequently been credited with falling in love with various actresses that he co-starred with in the past (before his ‘auditioned’ fake marriage with K Holmes.) It attracts media attention, takes the focus off his homosexuality, promotes the film and brings in more money, because everyone wants a chance to see him on screen with the (un)lucky lady & wish that their lives were just as glamorous. It’s time we realize that actors are playing in roles on and off the screen most of the time and the American public just eats it up. Leo is probably gay also, but the publicists insist on keeping the public in the dark ages (rather than moving us forward by giving us new role models) and the truth remains hidden.

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