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Jon Gosselin & Hailey Glassman: Horse & Carriage Couple

Jon Gosselin & Hailey Glassman: Horse & Carriage Couple

Jon Gosselin and his girlfriend Hailey Glassman share a passionate kiss as they arrive at the Oak Room by horse and carriage on Saturday (October 17) in New York City. The day after, the couple went for a a romantic walk in the rain.

Jon, 32, was recently ordered to return $180,000 he withdrew from a joint bank account he shares with estranged wife Kate Gosselin. The father of eight has until Oct. 26 to return the money or he will face contempt charges. Kate also has until that date to account for past expenses.

Jon & Kate Plus 8 will also wrap up in mid to late November.

10+ pictures inside of horse and carriage couple Jon Gosselin and Hailey Glassman

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65 Responses to “Jon Gosselin & Hailey Glassman: Horse & Carriage Couple”

Pages: [1] 2 3 » Show All

  1. 1
    Brendan Says:

    Ewww… still fugly, jon.

  2. 2
    Marieme Says:

    This dude’s just determined to hated. Might be the only thing he succeeds at.

  3. 3
    Lauren Says:

    Ugly ass dumb couple.

  4. 4
    Ali Says:

    creepy dude.

  5. 5
    Ruth Says:

    It this some kind of a joke? Who wants to see pics of this non talented and not attractive couple!

  6. 6
    coco Says:


  7. 7
    nicole Says:


  8. 8
    Suicidal Fish Says:

    I looooove that Jon Gross is so… gross because he looks exactly like my ex-boyfriend (which is also gross)!

  9. 9
    Jess Says:

    Jon makes me sick.

  10. 10
    kat Says:

    haha anyone else notice he’s smiling straight at the camera in most of these?

  11. 11
    n_n Says:

    Ohh NOOOOOO… another Heidi and Spencer!!!!

  12. 12
    katerocks Says:

    gag me.

  13. 13
    she shall remain nameless Says:

    #11, I totally agree with you!!! Bunch of fame whores. Jon’s the ultimate douche bag.

  14. 14
    SouthAfricanGirl Says:

    Jon and Hailey can be ‘in love’ all they want… but Hailey will always be known as a home wrecker!

  15. 15
    commonsense Says:

    @SouthAfricanGirl: It bothers me more that she’s a fool!

  16. 16
    miapocca Says:

    Hailey is not a homewrecker..she is an ANGEL who came to free the Kids and Kate from the douchebag!!

    Thank you Hailey!!

  17. 17
    Catalina Says:

    That poor horse.

  18. 18
    Louise Says:

    Just great, now I have to gouge out my eyes.

  19. 19
    Janet Says:

    Jon finally looks happy. He is enjoying life once again with out the control freak Kate!

  20. 20
    Jay Says:

    Yuck! Flaunting around just like he said he was embarrassed of a couple days ago. He can’t tell the truth if he tries. I used to think he was handsome. They way he took care of his family. Now not so much his entire persona has changed and his good looks are completely gone! Yuck!

  21. 21
    Betsy Says:

    Man, he can’t even kiss right. Ewww.

  22. 22
    Stephanie Says:

    can you please remove this. that picture makes me sick evertime i see it. no one cares about jon and his homewrecker.

  23. 23
    nan Says:

    What happened to Jon’s eyebrows?? They’re disappearing! Another couple of weeks and they’ll be totally gone.

  24. 24
    Mike Says:

    At least Hallie is not screaming and ordering him around like Kate used to do. All those criticizing him are obviously females who don’t understand the male point of view. If your wife/girlfriend is a shrew, emasculates you and disrespects you it’s only a matter of time until you will run into the arms of a woman who is the opposite. Get over it girls….it’s Kate that brought on this drama by her obnoxious behavior.

  25. 25
    *** JAMIE *** Says:

    sad how he thinks hes still 21. Middle aged men who run after young girls when they are married and have family responsibilities are the most pathetic creatures in the world.

    talk about a mid-life crisis

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