1. Just cannot help it – you MUST date douchebags, amirite Jess?

  2. Cock Dr

    A dress that squashes your titties and a date that looks like an dreadlocked undertaker is probably not going to get you on the cover of People.

  3. JimBB

    Come on honey, we have to get back to the 90′s or my white dreads will start to disappear.

  4. Beltliner

    She’s 33. She would’ve watched his music videos on MuchMusic when she was in seventh grade.

    I guess this gives hope to all of us who wanted to nail Liz Phair back in the day.

  5. He looks as if he has borrowed the suit from a (much larger) bellhop.

  6. Can’t decide if her dress should go down by an inch, or go up far enough to cover the face…

  7. Is that the guy who sang “Baby I love your Way?” Love that song.

    Jessica has a penchant for making herself look horrible most of the time. She needs to stop dressing herself and doing her own makeup.

  8. Who, with her boyfriend who?

  9. His hair looks like a poodles ass after it takes a dump outside, then the shit turns hard and crusty…OK That observation tells you much about life.

  10. “Step on it!… My Counting Crows cover band goes on in five minutes!”

  11. She doesn’t look so good in this picture, but damned if she doesn’t have a great pair of tits.

  12. Christ, I can smell that hair thru my computer screen.

  13. PassingTrue

    Obviously he dreds going out with her.

  14. Two Douchebags walk into a Bar, er ah, the Met

  15. Lily

    “Two water balloons in tube socks”, is how they recounted her boobs.

  16. …you know, i used to love droopy dog cartoons when i was a kid…

Leave A Comment