Lindsay Lohan with mystery man

June 12th, 2006 // 334 Comments
lindsay-lohan-and-friend-nyc-02.jpg
Lindsay Lohan
Lindsay Lohan
Lindsay Lohan
Lindsay Lohan
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Comments (334)

  1. tourettesguyswifeSHIRLENA | June 12, 2006 at 6:28 pm

    first fuck yeah

    Reply
  2. tourettesguyswifeSHIRLENA | June 12, 2006 at 6:29 pm

    whats with lohan always looking like she shops out of a dumpster… she’s got like bajillion dollars

    Reply
  3. mrs.t | June 12, 2006 at 6:29 pm

    Lindsay Lohan and Russell Crowe’s fat, gay, younger brother.

    Reply
  4. Iambananas | June 12, 2006 at 6:30 pm

    Lindsey Lohan and a really gay-looking man.

    Reply
  5. Iambananas | June 12, 2006 at 6:30 pm

    Which makes her a fag hag.

    Reply
  6. No_Angel | June 12, 2006 at 6:31 pm

    Why is she carrying that huge, ugly bag? It’s a wreck with the clothes she wears and drowns her in proportion.

    The guy doesn’t look too thrilled to be in the picture either. Maybe that’s why he’s stepping on her foot.

    Reply
  7. Iambananas | June 12, 2006 at 6:31 pm

    I think my 60 year old mexican gardener had those shoes… he wore them all the time.

    Reply
  8. waterranger | June 12, 2006 at 6:31 pm

    She looks so hot! Well, she does if you over look the granny sweater, oddly tapered jeans, adnm hideous shoes.

    But at least she doesnt have her rib cage showing ABOVE her boobs!!

    Reply
  9. mEGGSnBACON | June 12, 2006 at 6:35 pm

    oh god, that guy looks totally feminine.

    and um why are they *both* wearing skinny jeans? Jesus CHrist

    Reply
  10. mellymel | June 12, 2006 at 6:35 pm

    Really ugly bag, when did trash bags become en vogue? or is it just for trashy stars? He needs some help dressing as to not draw so much attention to his chubby belly!

    Reply
  11. BestNameEver | June 12, 2006 at 6:35 pm

    No, Lindsay, no!!! He’s got mips!

    (man hips)

    Reply
  12. hurley | June 12, 2006 at 6:35 pm

    he’s wearing girls’ jeans. and i can hear his sassy voice in my head.

    Reply
  13. Toonlite | June 12, 2006 at 6:36 pm

    he’s ugly…..but through Lohan’s Cocaine goggles…he looks GREAT!

    Reply
  14. Iambananas | June 12, 2006 at 6:36 pm

    #2.. nah, she’s only worth like 7 million, which is really poor. I mean, she lives in a hotel.

    Reply
  15. ShoNuff | June 12, 2006 at 6:37 pm

    What exactly is she doing with her right hand to the front of his trousers? Is she using the same death grip she’s using on her phone in the second photo?

    Reply
  16. jane's eyre | June 12, 2006 at 6:38 pm

    That is one creepy he/she. His face is guy (well, sort of) and his body is kinda feminine…I mean, that guy’s got a fat ass! Floopy, is my word for it. He looks floopy.

    It’s Pat!

    Reply
  17. Iambananas | June 12, 2006 at 6:39 pm

    Did anyone overlook the fact that it might just be a fan who got his picture taken with his idol? Which REALLY makes him gay. It might as well have been Barbra Streisand.

    Reply
  18. jane's eyre | June 12, 2006 at 6:39 pm

    And the skinny tapered pants (BLEH) don’t help his pear-shape.

    Reply
  19. Iambananas | June 12, 2006 at 6:40 pm

    jane’s eyre…

    If that guy has a fat butt,m so does Mary Kate Olsen… me thinks you are just a little too critical.

    Reply
  20. andrewthezeppo | June 12, 2006 at 6:40 pm

    She looks great, I’m glad she’s cleaned up her act…except for the whoring…cause everybody like a hot whore

    Reply
  21. waterranger | June 12, 2006 at 6:40 pm

    #17, if he was a fan, he would be standing BESIDE her, posing and smiling at the camera. right?

    Reply
  22. Iambananas | June 12, 2006 at 6:42 pm

    Not if he’s flamboyantly gay, #21. He could be striking his Movado-pose he fakes in the mirror twice a day.

    Reply
  23. Iambananas | June 12, 2006 at 6:43 pm

    He looks like a bigger star than she does.

    Reply
  24. honey | June 12, 2006 at 6:43 pm

    He’s probably just some guy who said “hey can I press my crotch up against you?” and she said “sure- go ahead, but you should know that I’m very discriminating and I don’t let just anyone press their crotch up against me. I’m practically a virgin- but, if you wanna fuck me- you can do that too.”

    Reply
  25. Iambananas | June 12, 2006 at 6:45 pm

    Well, #24… he’s gay, so I really don’t think it effected anyone.

    Reply
  26. Shelley Bonnechance | June 12, 2006 at 6:45 pm

    I think she stole my grandpa’s pajama shirt from the assisted living center.

    And that poor guy – his jeans. It isn’t hard to find jeans that don’t make your butt look weird and give you big enormous duck feet. And his hoodie is too small. A sartorial disaster, all around.

    Reply
  27. simone166 | June 12, 2006 at 6:46 pm

    does anyone else notice he looks like Perezhilton??

    Reply
  28. Iambananas | June 12, 2006 at 6:46 pm

    Both of them are disasters! Maybe if she knew how to dress herself, she wouldn’t look weird all the time. Maybe.

    Reply
  29. aivilo | June 12, 2006 at 6:47 pm

    That ugly man is wearing girl-pants. On the plus side, Lindsay’s hair is pretty.

    Reply
  30. EvilFiend | June 12, 2006 at 6:50 pm

    SOMEONE NEEDS TO TELL GIRLFRIEND THAT HE DOES NOT LOOK GOOD IN THOSE JEANS.

    Reply
  31. Iambananas | June 12, 2006 at 6:50 pm

    That buy in the background with the hat looks like Putty from Seinfeild.

    Reply
  32. RichPort | June 12, 2006 at 6:52 pm

    What the hell is my coke dealer doing with this bitch??? Oh….

    Reply
  33. jane's eyre | June 12, 2006 at 6:52 pm

    22
    Speaking from experience?

    Reply
  34. jane's eyre | June 12, 2006 at 6:59 pm

    And he has man-boobs.

    Reply
  35. jane's eyre | June 12, 2006 at 7:01 pm

    AND WHAT’S WITH THE SCRUFF? WHY DO GUYS THINK THIS IS A GOOD LOOK? Very few guys can pull the scruff look off, and he is not one of them.

    Reply
  36. limper | June 12, 2006 at 7:04 pm

    That is an impressively ugly bag Lindsay is holding. It looks like something a mad scientist would carry a human head around in.

    I think she’s lugging that horrible purse around as a diversion to keep people from noticing she’s dating a retard.

    Reply
  37. limper | June 12, 2006 at 7:05 pm

    #32 wins the thread so far, BTW

    Reply
  38. PelvicBoogie | June 12, 2006 at 7:13 pm

    Lohan: “You said you had some coke in your pocket, you ass.”

    Dude: “Oh, it’s there, just keep digging.”

    Reply
  39. Skrpune | June 12, 2006 at 7:17 pm

    What is with the Pippy Longstocking personation? UGH those loose braids have to go!!

    Reply
  40. Ari | June 12, 2006 at 7:19 pm

    35– I actually really like most men with some scruff. I like the way it looks and the way it feels.

    However, this guy could have his picture taken while screwing some woman, and he’d STILL look like a flaming homo. A little scruff isn’t going to help the massive gay-vibe he’s got going.

    And he DOES have a big ass. A big, round, feminine ass. Looks like it belongs on Oprah or something. Ew.

    Reply
  41. Skrpune | June 12, 2006 at 7:22 pm

    DOH, I mean IMpersonation. Damn.

    Reply
  42. jane's eyre | June 12, 2006 at 7:23 pm

    Well Ari, to each his own. When my husband goes without shaving for a day, I avoid kissing him, because I don’t like to have my skin sandpapered off. I’m such a delicate flower, you know.

    And even though I think Colin Farrell is a skank, I think he looks good with scruff.

    Reply
  43. chanel_bear | June 12, 2006 at 7:34 pm

    surprisingly she actually looks sober…i mean, decent in this picture. but somebody needs to tell that dude that a) people with huge butts should not wear skinny jeans, and b) men should not wear skinny jeans.

    Reply
  44. Nikk The Templar | June 12, 2006 at 7:35 pm

    I bet if I threw a bucket of water on LiLo, she’d melt.

    Reply
  45. plymouthrock | June 12, 2006 at 7:39 pm

    The guy is thinking “Does Linsay make my butt look big?”

    Reply
  46. Ari | June 12, 2006 at 7:39 pm

    42- Yeah, it’s a personal preference. *shrug*

    Reply
  47. MP$40 | June 12, 2006 at 7:52 pm

    #32 – Rolling on the f*cking ground! That was damn funny!

    #16 & 27 – You all aint right! HA!!!

    #38 Wins the ‘caption this’ contest

    Besides, she looks like she just got back from shopping at the Salvation Army. That outfit sucks.

    Reply
  48. jane's eyre | June 12, 2006 at 7:55 pm

    I have no idea what
    “You all aint right! HA!!!
    is supposed to mean.

    Reply
  49. jane's eyre | June 12, 2006 at 7:55 pm

    46
    Just like some people prefer phallic fruit.

    Reply
  50. jane's eyre | June 12, 2006 at 7:57 pm

    I bet if I threw a bucket of water on LiLo, she’d smell like the bathroom at the beach.

    Reply

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