Top Stories

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

Just Jared on Facebook
jon gosselin hailey glassman horse carriage 01
jon gosselin hailey glassman horse carriage 02
jon gosselin hailey glassman horse carriage 03
jon gosselin hailey glassman horse carriage 04
jon gosselin hailey glassman horse carriage 05
jon gosselin hailey glassman horse carriage 06
jon gosselin hailey glassman horse carriage 07
jon gosselin hailey glassman horse carriage 08
jon gosselin hailey glassman horse carriage 09
jon gosselin hailey glassman horse carriage 10

Photos: Arnaldo Magnani/Getty, INFdaily
Posted to: Hailey Glassman, Jon Gosselin

JJ Links Around The Web

  • Tom Cruise says Top Gun 2 is in discussions - US Weekly
  • Miley Cyrus campaigned for Hillary Clinton at a college! - TMZ
  • Kristen Stewart really cares what people think of her - Gossip Cop
  • Little Mix officially have another #1 single! - Just Jared Jr
  • Richard Simmons is closing his down his famous LA exercise studio - Radar
  • George Clooney got a visit from his adorable pup on set! - Lainey Gossip
  • Deadpool 2 director Tim Miller has stepped down - The Hollywood Reporter
  • Brendan

    Ewww… still fugly, jon.

  • Marieme

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

  • Lauren

    Ugly ass dumb couple.

  • Ali

    creepy dude.

  • Ruth

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

  • coco


  • nicole


  • Suicidal Fish

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

  • Jess

    Jon makes me sick.

  • kat

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

  • n_n

    Ohh NOOOOOO… another Heidi and Spencer!!!!

  • katerocks

    gag me.

  • she shall remain nameless

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

  • SouthAfricanGirl

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

  • commonsense

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

  • miapocca

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

    Thank you Hailey!!

  • Catalina

    That poor horse.

  • Louise

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

  • Janet

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

  • Jay

    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!

  • Betsy

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

  • Stephanie

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

  • nan

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

  • Mike

    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.

  • *** JAMIE ***

    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

  • haasy0988

    does this guy ever not have a cigarette or a cell phone in his hand???
    he is such a looser

  • haasy0988

    does this guy ever not have a cigarette or a cell phone in his hand???
    he is such a looser

  • haasy0988

    so funny how he states the complete opposite on media shows, he is a trip, one day these kids will realize what a schmuck their dad is. Poor kids, how embarrasing for them that their dad hangs his junk on his sleeve, really jon do you think this relationship will last forever? Is it really worth parading around like this to sacrifice your kids? Must be, these are things you will most likely regret, who knows though, you have shown the world some strange things about yourself, Kate is looking like Mother Theresa…

  • Janet

    Keep in mind that while Jon (the bad father as some of you call him) was raising those kids, Kate was running around the country with the body guard. Those 8 kids don’t have a snowballs chance at growing up in a decent home. Their mother is all about the almight dollar and don’t give a crap about those kids. Would be nice if they could be adopted out to a good home.

  • Lisa2

    Why are you all bashing on Kate??? She is the one that is making money for the family. So what if she has to travel to make money for the family, at least she is doing what she can to give her family the best she can. If she was a man, none of you would be complaining if she had to travel for a job. Also, if she had a regular 9-5 job she would be gone more than 40 hours a week (with driving time, which you can add maybe another 7 hours a week depending on the distance). Also not to mention she would still have to run errands to take care of her 8 children. Since now she is the main caretaker now she not only has to make a living, she has to take care of all her AND Jon’s kids basically herself. Just think how you would feel if you had to do this all on yourself and earn a living and deal with such an ass of a husband/ soon to be an ex-husband. I don’t have a problem with Jon dating, but my gosh can’t he wait until the ink is dry on his divorce and focus on his kids and their wants and needs? He is always want’s to play the victim, when he gets bad press, but then doesn’t do anything different to make himself better??? What a LOSER!

  • Shelly_2

    I knew I shouldn’t have looked at those pictures – my breakfast nearly came up. Hailey really rocks those green Converse – the kind my TWELVE year old wears! LOL I really hope Kate takes Jon to the cleaners and that he really really has to pay for hacking into her bank accounts and emails. That’s about as low as you can get.

  • Shelly_2


    LOL Classic!!! Thanks for the laugh this morning!

  • Karen

    quit covering this disgusting ASSHOLE! and his Bee-atch!

  • wandeela

    I always wondered why Kate was so mean sometimes..I figured it was all those kids..but now I realize that it was JOn..being a horses end…he really makes me sick

  • VanM

    Hailey is going to stay with Jon because she is a wannabe….Any attention even negative attention is ok with these two disgusting media whores. And i’m betting Jon has sold his soul to the paparrazi because he needs the money…

  • VanM

    ooohhh Please Janet….While Kate was running around…She was out making money for the family although I give you props for trying your best to try and make JOn look innocent. Where is the proof that she is or has ever had an affair with Steve of anyone??? Kate was mean to Jon but Jon was also an A**hole too. I never saw Kate as being the perfect wife?mother but she has always done everything for her kids. Jon couldn’t even hold down a job for more than a few months and he was all to eager to stop working so that Kate could go out on book tours and speaking engagements. Jon created his own nightmare and now he is going to pay for his cheating, lying, and thieveing ways……

  • Adam

    GO JON BOY!!! Funny how the gals complain and say how much they hate him, but yet they still click, read and post. he does make money out of this you a holes. Don’t like him then move on!!!!1

  • VAN

    At least she is wearing appropriate shoes in this weather other than his fugly wife still wearing open toe sandals in the freking rain and cold. If Katezilla isn’t careful her little piggies will freeze and fall off.

  • Richard

    Man, this dude is an idiot.

  • VAN

    Wheres Katezilla? She must be getting ready for Halloween, sportin that fugly hairdo.

  • Jody

    WooWeee…at least he has found some happiness. His itchy ex still can’t find a decent hairstylist

  • Sam

    Real DumbAss & his SKANK!!!!!!!!!

  • I’m so broke.

    I am not fan of Kate and don’t see how you Kate fans see the good about her that is cleary not there.
    That being said,Jon is far worst. Dumb. Who advises this guy? From taking the money in the joint carrying on with thisbong smoker fan, to getting fat,to he is just a mess.
    Does jon even realize he lost it all?
    The fame.He is now infamous.
    The tv show.No other show is going to pick himup.
    The money. HE did not make as much as Kate. He can still get a portion off of the marital assets which are the kids, but Kate will probably stop that being that she has made enough money of the kids and can do her own thing now.

    Fame and fortune were most impt. to Jon and Kate.
    When people seek fame and fortune, some can handle it and some can’t.
    Kate has fame and fortune thanks to he legion of misguided, ignorant fans. Jon has nothing.
    Kate fans and fans of the innocent 8 kids,you’ll love the show of the kids having problems mess in a few years.

    Those poor kids. Half of a mom and noting of a dad.

    PLEASE do not support this trainwreck of Kate,Jon or the innocent kids who need a normal life for once in their lives.

  • I’m so broke.

    Kate -a nsuccess in fame,fortune.
    Jon-a success in dumbness.
    the kids-a failure.

  • Moon

    @miapocca: She is a homewrecker and she looks like a hooker that he just picked up off the street!!!!!!

  • Janet

    Going around the country with some body guard watching over you is NOT working! My mother in law raised 8 kids and never had to leave to promote a book or to film a talk show. Kate has ruined those kids lives and they will realize it when they grow up. For those of you that don’t like Hailey or Jon or what they are doing….you really don’t have to. Those two are having the time of their lives while “little miss whiner” is trying to make everyone think she is at home taking care of the kids. Where are the kids when she is on all of these talk shows crying because she can’t pay her bills??? She is a money whore and her kids are her employees! Sick! She doesn’t deserve to have kids. She needs to get a real job and help support her family like the rest of us have to. Quit blaming Jon! The only thing he is guilty of is having the fun and good times that his wife never gave him! Kate is a wonderful mom…remember the episode where she sent her kid to the doctor with the baby sitter? That is NOT a good mother. Sure Jon has his faults but Miss Diva is definitely NOT a saint.

  • vince

    Jon is cool, like sooo cool compared to his snobbish, fugly looking ex. She always appears itchey and thinks she is all it cause she is a fame reality whore

  • sammy

    Ughhhh, she looks sooo much better than his fugly looking ex.

  • addie

    Katezilla is at home crying to the 8 kids cause her reality is that TLC ran off and took their equipment with them…lmao

  • Janet

    Since the show was supposed to be all about the kids, why don’t they just start a series with the kids. The first show could be called “Jon & Kate got ATE” and it could start with a Godzilla creature devouring those two. After that the series could entail the baby sitters (they are raising the kids anyway) and the kids. How great would it be to never have to deal with Jon or Kate again?

A Member of Townsquare Entertainment News | Advertise here