Jessica Simpson and John Mayer break up for good

June 6th, 2007 // 60 Comments

Jessica Simpson and John Mayer have broken up again – this time, apparently, for good. A source close to Mayer says: “It has been rocky and it had been rocky, and it reached the end of the road. It is definitely over – the relationship has ended.”

A source close to Simpson confirms: “They broke up Sunday night, but who knows what the future will hold. This is the twelfth time they’ve broken up. Their relationship is volatile. Last week they felt better than ever. This week, things are rocky. Who knows what the future will bring.”

These guys are on and off again so often there’s no point even talking about it. By the time I finish this sentence they’ll already have gotten back together and broken up like seven more times. Which is slightly more than my relationship with Jessica Alba. Look, baby, it’s over. The late night calls pleading for just one more night of ravaging are getting creepy. Have a little dignity.


  1. didey23

    silly girl

  2. RichPort

    I get where he’s coming from… the last time I had to share an ex with her dad was torture. After fucking her for a few months, I was sick of her saying “that’s not how daddy does it…”

  3. Jezzica==girl thank God
    that zhit iz over…..
    U don’t need hiz old gray
    ballz, I’m gettin sick juzt
    thinking about them…
    Cheer up and get your shit
    together, U don’t need a
    daddy type to screw…..
    therez plenty of other
    dickheadz out there..

  4. Danklin

    Whats the point of dating after you’ve broken up and gotten back together this many times? That would make for a hell of a marriage. Maybe John didnt really end things. theres no telling what he says half the time.

  5. imran karim

    is she wearing a towel?

    imran karim

  6. Poodlesaremanly

    I love how he broke up with her while holding a poodle. How manly of John. He’s a beast.

  7. She seems like the kind of chick who probably breaks down into tears at least 3 times a day. No hot amount of hot cans are worth that.

  8. wedgeone

    He was waitin’ … waitin’ on the girl to change.

  9. WowJustWow

    Oh snap! He took the dog too.

  10. wedgeone

    Bern – crazy DMBS, but the dialog – you sound too much like Mr. Fish. Cut that out.

  11. wedgeone

    This one isn’t Jessica’s fault. John finally realized, after years of begging girls to chafe his anus raw with strapon dildos, that he really loves something: thick ropey salty semen, shooting out of a cock that was just in his ass. The gagging, the tearing of the eyes, the sudden spurting, the hand at the back of his head to force his mouth down juuuuust a little too far…heaven. Just a little piece of snort-glug-yak-glug heaven. The ladies know what I’m talking about.

  12. lawpunk

    How on Earth JS continued dating a guy that looks like Edward Scissorhead for this long is beyond me. He is one ugly dude. She must have some real low self esteem, which means many dudes here might actually have a shot with her.

  13. PoorJessica

    These pics made me feel really really bad for her. Give her a break, John: it’s not her fault that she is so dumb. Growing up, her dad probably kept feeding her his cock instead of real food with protein.

  14. jaxx

    seems odd as john is on tour (in idaho on sunday)

  15. He’s mad because she’s been spending so much time at my house.

  16. cosmetologis

    Who needs him.

    Spit, Spit, Spit!

    She should just go out and get another puppy. A Golden Retriever puppy would be the best choice. I love puppies.

  17. MissGreen

    Dude, this is old news. Those photos came out sometime last week. You need to get with the program!

  18. pinhead

    You got penisbutter in my chocolate!

  19. jenster

    i think its great that this ugly big headed freak show of a guy is like “breaking her heart” hahahah poooooor baby, look how serious and intense he is, then a pic of her
    sitting all alone, weeping bitterly.

  20. 1seekspie

    Part of me wants to feel bad for Jessica because she’s a human with feelings and everything, but it’s just so hard to feel sorry for a person with a lot of money and an easy life whilst so many people in this world have to suffer.

  21. copyofblueboy

    He was saying “Jessica, no matter how hard you try, you will never be as smart as this dog.”

  22. PoorJessica

    40 – Your comment made tears flow on my cheeks, both from laughing so hard and feeling bad for Jessica at the same time…

  23. Yeah, did anyone honestly think they’d last?

  24. Jessica

    John, I’m very upset. I asked my sister and she’s really really smart and she said there’s no such thing as the “cum fairy.” So I’m asking you again: why is there always cum dripping out of your ass when you get home?

  25. copyofblueboy

    PoorJessica…you are a better person than I am. I don’t feel sorry for her in the slightest. She looks like Ricky Martin in drag and she’s dumber than a box of hair.

  26. Wedgeone

    #40 – Exceedingly funny!
    #30 – it amazing that I can post that much material in less than one minute!
    Doesn’t it suck Mr Troll, when all of the fucked up effort goes to waste because I posted just before you did.
    Take that, thunder.

  27. Wedgeone

    correction: it’s amazing

  28. frenchie


  29. DEL


  30. Greatestntheworld

    I would never break up with Jessica Simpson because I would have never allowed myself to be sucked into a relationship with a girl with a negative IQ. If that’s picky, then I am proud. I can’t stand ugliness or stupidity.

  31. woodhorse

    xoxoxo Wally,
    whether gallant and slashing
    or cold and ripping
    I always have to catch my breath

  32. woodhorse

    xoxoxo Wally,
    whether gallant and slashing
    or cold and ripping
    I always have to catch my breath

  33. woodhorse

    and I thought Typekey was bad, excuse the double post.

  34. ksea

    Look it is all bullshit John had his hair like that in 2004 I saw him in April and he doesn’t even look like that anymore. Besides you can’t take trash like her back to CT to meet mom. Get real!!!

  35. msatt kkkk

    haha first thing he said at his concert on saturday june 2nd…
    “so whos sleepin’ in my tent tonight?!”

  36. hungmaster

    Jessica: how come they’re called buffalo wings, they can’t fly!

    Jessica: Why is it called Chicken of the sea, Chickens can’t swim!

    Hey Jessy Bitch, stick to what you do best–spread your legs for me, nobody takes you seriously as a person and as an actress! Your dumber than my pet rocks. Wait a minute, they might be smarter!

  37. lou

    Goes to show you, even if a chick gets DSL plastic surgery, it doesnt make her pro. I like the pictures….wonder how that conversation went:
    John: yo jess last nite BJ was pretty bad u used teeth on me again
    Jessica: I am sorry john I am still getting use to these lips
    John: yah your lips are like getting in way of my music
    Jessica: what are u trying to say
    John: no more bad BJ and no more J.S… your sister available?

  38. gareth

    Isn’t he doing that dude from Maroon 5 now?

  39. Jodi

    Finally.She is such a dumbass.Most intellegent men like women with a higher IQ of 10.

  40. Tell me how you can’t feel sorry for this sad face?…

  41. Rachel

    i feel bad for jessica. she’s so fucking beautiful and all guys do is treat her like shit. ah- to find someone with the same problems as me….jk

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