Jessica Simpson and Owen Wilson spotted together

November 1st, 2007 // 50 Comments

A spy for Star magazine spotted Jessica Simpson and Owen Wilson out together over the weekend. The two met on the set of a Willie Nelson video a few weeks ago and seem to be hitting it off, according to NY Daily News:

The two dined Sunday at the Huntley Hotel in Santa Monica before retiring to his Malibu home.
“He couldn’t keep his hands off her,” a witness tells the mag.

Don’t you dare break his heart, Jessica. That man’s been through a lot. What he needs right now is someone to make him appreciate the good things in life. Why, yes, your breasts would be one of those good things. I mean, I wasn’t going to bring them up unless you did. Your dad does it all the time? Ha, that is funny. You are funny. Say, you want to get a drink? Oh, don’t worry about Owen. He’ll be fine. He does great with rejection.


  1. firster

    fucking first

  2. cookie monsta

    think of the nuclear scientists these two could breed ….

  3. kiki

    you’re going to hell. just my instinct, but she can’t keep a man. she’s a lesbian. just like spears.

  4. The butterscotch stallion rides again! Owen’s legendary salad tossing skills will be put to the test, pushing his tongue to the very limits of human endurance. Hey! Is that Kid Rock with mostly empty bottle of cheap bourbon?

  5. Mar

    Perhaps he can introduce Jessica to a wonderful thing named suicide.

  6. rooster54

    i think somewhere within jessica simpson’s vast knockers, lies a key to the cure for depression. They’d make a great couple.

  7. imran karim

    she changes from looking hot to not daily

  8. RENEE Z....

    He’s gonna go into shock going from Kate’s flat chest to Jessica’s bazoongas.

  9. iburl

    Chestal Prominations. Excelsior!

  10. Igottabemeee

    I agree with #12. Those enormous mammaries might be too much for him so soon after his breakdown. He should have one medium-breasted rebound girl in between. We can only hope the meds with keep him grounded.

  11. That apricot colored, form fitting dress goes so well with her blond hair and coloring.

    she has gained a little weight, but on her it looks flattering

  12. Nothing like a young hot dumb big breasted blonde to help the depression. The shrink that prescribed this treatment is a fuckin genius.

  13. Dating Hot Girls in your Area


    Enjoy !

  14. Jessica is a whole lot of woman for one man to handle. Remember poor Nick Lachey? Remember how he moved to this walking corn belt to a string of random swarthy hotties? Hell yeah. Nick Lachey – hotter than the Owen. Though I’m sure one look in those melty puppy dog suicidal eyes of his makes Jessica’s enormous breasts go all aflutter with throbbing biological clocky goodness. Serious, how long before this moo-moo is pregnant. her boobies + fluffy nut could save the world, but she will probably waste all that earth mother goodness on a dane cook jr or something.

  15. Ript1&0

    It’s Halloween and I’m RIPT out of my head and I danced all nite with my bra hanging out. Good times.

    Jess should get him an “I’m such a loser I couldn’t even kill myself” t-shirt. I always wanted to do that for my friends that tried…

  16. Mr Semprini

    What in the name of Vader is going on with her feet? Man, looks like they could kill ya… Heyyyy….

    If anything happens to Owen, Jess did it!

  17. ph7

    I guess he took the advice of Little Miss Sunshine’s grandfather:

    ‘Fuck a lotta women kid, not just one woman, a lotta women. …’

  18. She’s a man. Kate Hudson is prettier.

  19. the one and only me

    She has two things Kate Hudson does not……..a creepy dad and Forrest Gump’s IQ.

  20. my comment

    She looks good here.

  21. JP

    OK, I give in. I have finally decided that I will have sex with Jessica. Nasty, hardcore, brutal sex. So, Jessica, hit me up and I’ll show you how to use those titties. Thank you.

  22. Gerald_Tarrant


    I’ve always wanted to get folks those shirts too.

  23. BIG

    She just has that all American girl look to her. Outstanding big tits and a nice plump ass. Three cheers for big tits.

  24. lg

    I hope he wears asbestos condoms…

  25. toolboy

    I could hit that, but only if she promised not to talk….ever.

  26. havoc

    Hey, they’re both Dallas peeps, why not? Plus those fun bags would provide hours of entertainment.


  27. sportsdvl

    Might as well date someone who’s brain committed suicide.

    Oh, #1 – you are a loser.

  28. She has the greatest casabas ever.

    And if you don’t agree, you’re gay.

  29. Who wouldn’t have a hard time keeping their hands off her? She may be dumb as dirt, but she has a hot body

  30. You know what they say? Sooner or later losers are always finding themselves in others!! So it’s not necessary to call the names of owen “pinokkio” wilson and BIG-TIT-SISTER simpson apart!!

  31. Jen

    Imagine the noses the hypothetical offspring might have? Gack.

  32. #33 Nope, pretty sure dirt is smarter than her.

  33. Mike

    #35, damn you beat me too it… although I was gonna use the funnier word “schnozzles”.
    Gives me nightmares just thinking about the schnozzle on their offspring.

  34. Call it what it is

    “before retiring to his Malibu home.”


  35. JESUS CHRIST, Your looks are so Naive and Dumb. I’m glad this action confims it!! How fully loaded your TITS are, so empty is your head, AMAAAZING!

  36. endoftheshityear

    Jess is at least 25 percent AmerIndian

    someone get a swab and perform a DNA test, pronto

  37. Another Easy Booty Call for the Famous

    Hmmmm…… Owen made a good choice of getting an easy booty call just like John Mayer once did.

  38. PunkA

    Jess hit the wall. She peaked about 18 months ago. It is all down hill for her now. The stupid pin cushion. I mean, John Mayer? Seriously? Like dating Edward Scissorhands. And now The Buttscotch Stallion, who apparently has issues with drinking and life. Like I said, downhill.

  39. havoc



  40. tanya

    Jessica: “My daddy says I have nice jugs”.

  41. Spongebob Gangsta

    I hope Owen asks her dad if HE has an STDs now that he’s with Jessica

  42. scooby

    her face is a little messed up but man she has some awesome tits. what the fuck.

  43. FlyOnTheWall

    Heres what happened at dinner:
    Jessica: So you like really slit your wrists?
    Owen: Yea Baby I was going all the way.
    Jessica: Could you help me go all the way?
    Owen: Before or after Dinner?
    Jessica: After.
    Owen: My place or yours? My parents are home.
    Jessica: Mine.
    Owen: OK

  44. Auntie Kryst

    OK, I used to say all you pukes were wrong about her. I found her smoking fuckn’ hot. Stupid? Oh fuck yeah, but dynamite body. Now I’m starting to see the dude face. Also @42, nice comment.

  45. V

    Ok, so, looks like the cure for suicidal tendence is banging brainless bimbos with huge breasts and blonde hair.
    Note to me: don’t forget to buy milk, bread, orange juice… oh, and razorblades.

  46. selina

    she is preety in this green dress, i like her hair style. i heard that sh ehas a account on a millionaire & celebrities site called, i do not know it is true or not.

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