Jessica Simpson dates Quasimodo

August 30th, 2006 // 69 Comments

jessica_simpson_john_mayer.jpgPeople magazine reports that Jessica Simpson is dating John Mayer despite the scientific evidence suggesting he may, in fact, be the ugliest man on Earth.

“She’s tiptoeing back into the dating world,” a source tells People. “It’s the first stage. She’s never been happier.”

I can’t tell if this is worse than James Blunt dating Petra Nemcova. They’re both anomalies of nature, but I fear this time God has gone too far. He might as well start mating horses with rhinoceroses. Although that might actually be kind of cool because their offspring would probably be unicorns. And just cause, here’s Jessica Simpson at the release party of her new album yesterday, where she lost her voice and had to postpone a TV appearance.


  1. dupababy

    you know back in the days before chestica underwent her record breaking 6,999 hours of plastic reconstruction, she was actually the brother of john mayer.. this of course explains the closeness in not only their relative appearances but also their charm and charisma.. looking at these two conjures up all the excitement of watching the freaking grass grow.. only at least watching the grass grow is a constructive utilization of time..

    after praising the supreme being of kindness that limited her voiceless yesterday, it appears chestica’s plastic is more superstrongpowerful than anything else in this or any other world.. look up in the sky, it’s a bird, it’s a plane.. it’s SUPERSKANK!

  2. RichPort

    I guess David Spade, James Blunt, and Shabba Ranks were already taken. She’s got the self esteem of a suicidal manic depressive bulemic…. I mean Nicole Richie.

  3. You can’t fool us. That’s obviously a wax figure.

  4. biatcho

    the last time I sawe a mouth like that it had a hook in it (thanks Rodney!)

    Seriously, she is retarded. And has crinkly upper thighs… can I get some cottage with my cheese please.

  5. chortle

    Think the attraction on John Mayer’s part is her inability to speak? Jessica may want to incorporate laryngitis into her search for her 2nd ‘Mr. Right’…

  6. BLucky

    Ewww. At least Dane Cook looks f*ckable.

  7. howlingatthemoon

    Yes! I always hoped this would happen!

  8. nina

    i must admit, i am one of the women in the united states that think john mayer is the sexiest man alive (but i don’t wear tank tops and have highlights in my hair year around) it’s strange, he doesn’t photograph well… and obviously he has a thing for chesty women (ie jennifer love hewitt) and that it doesn’t matter if they used their brains to up their cup size…. because he isn’t dating jessie baylin ( i wondered why for a while.. she is pretty, smart and talented… but then i realized why……

    her breasts are non existent.

  9. biatcho

    She’s look like a white version of one of those Williams’ tennis beasts. The dress that doesn’t fit, the mouth of an ape, the thighs of a thundercat and the head that just isn’t proportional to the rest of the thing.

  10. MyWellRehearsedMistake

    Nah, there’s no way someone as dumb and vacuous as Jess would date this ugly dude. To be fair, the media have linked this girl with every man she’s been within a mile off post-Nick. I’ll believe it when I see the MTV series “Joe Simpson’s Whoring Out his Daughters Again Part 453637″

  11. jrzmommy

    I thought Andre the Giant was dead? What? That’s not Andre the Giant? It’s John who? Who the fuck is John Mayer and why is he trying to smother Jessica Simpson?

  12. combustion8

    Would it kill her to use a bowflex once in a while.

  13. DrDanny

    Lighten up, fish. Mayer is a normal looking guy. I’m not saying he doesn’t deserve to be picked on, but you’re barking up the wrong tree here. And he’s smart too, so maybe he’ll rub off on Ms. Simpson. (Which sounds like fun, actually.)

  14. jrzmommy

    What the fuck is that gay-assed over-the-shoulder open-mouthed annoying-as-fuck pose in the last picture? What the fuck? Is she some kinda WWII pin-up? God that is so fucking annoying and gay I hate it!

  15. RichPort

    It’s well known that ugly guys have huge cocks. I for one can scare the wings off a fly, but I’m hung like a fucking African elephant.

  16. The Devil's Prom Date

    I hope Nick Lachey RUINED that ass.

  17. alaskanchicsickle

    Maybe these girls are having a weird competition on who has the ugliest boyfriend. I think Petra is still in the lead. I admit John Mayer looks kind of fug in pictures, but in person, he’s adorable.

  18. biatcho

    #15 – like one of those 5-legged african elephants I am so fond of? sweet…

  19. bigponie

    that disgusting mouth, to think that nick use to be in there showering that crater with his paste.

  20. yuckyfresh

    she’s big-boned.

  21. commissioner

    That dizzy blonde is slowly morphing into what we, in this part of the country, call a “partied out whore”.

    Someone should have told her you should never “trade down”. No way would I have tossed that smokin’ hot Nick away for some bloated, miserable looking average guy. (Who is wearing too many fucking shirts.) He should have put one of those kicky polos over his face.

  22. yuckyfresh

    #17 – petra is also in the lead because she is WAY hotter then jess. that makes the gap even bigger….

  23. yuckyfresh


  24. As she gets less and less famous for anything other than being a tabloid sotry her shorts keep getting shorter and shorter…..hmmm,

  25. yuckyfresh

    pic #3 – “i lost my gym membership” :(

  26. jrzmommy

    “I Lost My Virginity (to Dear Old Dad)”

    Again with the annoying gay faces. I wish Superfish would do some sort of montage of her gay faces and Britney’s gay shopping faces.

  27. popegoestheweasel

    I dunno, I think James Blunt is a lot prettier than Jessica Simpson LOL

  28. RichPort

    #18 – 5 legged indeed. It sucks because I’m an easy target for poachers, being that I leave tracks that look like this:


    I hang a bit to the right…

  29. I don’t know, I think James Blunt is a lot prettier than Jessica Simpson LOL.

    Wait, did somebody just type that? Oh man. Boy do I feel stupid.

  30. Wait, she lost her voice? Then the news isn’t all bad.


  31. Damnit, I with I would have know a few years ago that she was in to really ugly guys with giant penis’s, I would have totally nailed her.

    That just goes to show that even the ugliest rockers get the poon.


  32. PS – that last picture is what she will look like on our wedding night, as she gets a little “angry ferret” action.

  33. LOL.

    What the hell is wrong with John Mayer?

  34. MyWellRehearsedMistake

    32. Angry Ferret – I love your blog. Made me laugh very loud and now people are looking at me funny…

  35. AshGurl2897

    He is kind of hideous. You expect him to be adorable, but he’s not. His music is decent. They are a bit mismatched and I doubt this will last more than .5 seconds (if it is even true).

  36. radically4peace

    I don’t think John Mayer is that bad. That pic makes him kind of look a little tubby, but he’s pretty average looking in my opinion, not hideous.

    And she has a really big head. She looks like a giant Q-tip. Have you ever noticed that?

  37. saltpeanuts

    Some of you are crazy. I would eat Jessica’s vag until my lips fell off.

  38. onesunnyday

    How could she possibly pick him over Nick Lachey? It just..makes no sense..

  39. Mojogirlie

    What is wrong with you twats that think Nick Lachey is good looking?? Blech.

  40. James

    Having a bad look day there huh John Mayer. Chestica as she was so interesting called has one plus at least she sticks to her own race, so far….

  41. jrzmommy

    “She’s never been happier!” Not even when she was the star of her own show, married to a reasonably attractive guy, and on the covers of magazines for all the right reasons. NOOOO she’s thrilled that her ex is fucking a goddess who was her friend and her only steady date is her fag hairstylist. Never fucking happier.

    By the way, what is that grimmacing at us on the ‘Got Gas’ ad on the top right of this page?

  42. With all that money homegirl has she should lay off the collagen and invest in a Thighmaster. She needs to stop doing naughty things with that mouth if she doesn’t wanna lose her “voice”.

  43. sookie

    what is wrong with John? He is way too good for her. I was disgusted when I heard about this.
    have to disagree about his looks-he’s a hottie!

  44. Hey, John Mayer is a good guy. He does good music and will on the Dave Chapelle show. If anything, Jessica may be too corny for him.

    Besides ugly guys and beautiful girls is the latest thing. All of you should be happy!


  45. biatcho

    #41 – thank you for noticing the got gas chick too. almost made me barf a lung yesterday.

  46. jrzmommy

    biatcho–just wondering what you think of the apology yesterday? it’s the weirdest thing, it’s a totally different person. we were just talking about it on the pee diddy thread.

  47. jrzmommy

    “Jessica Simpson says she knows she has a hit if her mother likes a song.

  48. Italian Stallion

    Instead of singing “Wonderland”, I guess he’ll sing his new one to her “Wondering”

    “Your fathers been wondering”
    “Your father say’s he wants some head”
    “Your fathers been wondering”
    “Your fathers been wondering where you’ve been”

  49. The Pharoah

    I sincerely hope that all comments berating Jessica’s looks are jokes. My god she is fucking gorgeous. Thighs unbelievably hot. Also, Wendy–Jessica doesn’t need a thighmaster. Maybe, homegirl will use some of her money to buy you some glasses that you apparently need for your vision and cock-eye.

  50. DuluthDawg

    I’m telling you…no matter how ugly or stupid you are, if you play guitar well, you will land yourself some seriously quality poon.

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