Jon Gosselin’s girlfriend seems classy

July 15th, 2009 // 155 Comments

Seen here in photos taken from her Facebook page and passed around the Internet like the blunts she enjoys lighting, Hailey Glassman is apparently using her relationship with Jon Gosselin to get famous, according to Us Weekly:

Glassman — whose father performed Kate’s 2006 tummy tuck — has tried out for MTV’s Real World and Oxygen’s Bad Girls Club.
“I think after realizing she had a connection to Jon through her father and that Jon and Kate’s marriage was rocky, she saw an opportunity to get famous,” one of Glassman’s pals tells Us.
James Appleton, who describes himself as her “hookup friend,” tells Us Glassman dropped him abruptly just before news of the pair broke.
“A couple days later a mutual friend was like, ‘Oh hey, your girl Hailey is pretty famous. She’s dating this older guy who has like eight kids,’” says Appleton, who met her during a 2007 spring break trip to Acapulco, Mexico.

Jesus. Could you imagine if this chick makes it on to Jon and Kate Plus 8 and puts that on her resume?

TV EXEC: Ms. Glassman, it says here you were on Jon and Kate Plus 8. Can you tell me about that experience?
HAILEY: I vomited on eight small Asian children then burnt their playhouse down smoking a J with some guy I banged outside Denny’s.
TV EXEC: …. Welcome to the Real World.
TV EXEC: Whee!
HAILEY: Do I still have to give you that BJ?

The End.


  1. She is epitome of head on the first date… before dinner…

  2. jeana


  3. facking luzr

    Photo # 5 = FACE PLANT!

  4. Jackie

    It looks likes Kate is winning in this break up.

  5. Katie

    This bitch is so nasty and fake but hell YEA! smoke that weed!

  6. Nelly

    How is Kate winning? Jon went from a 30-something annoying bitch with 8 kids to a 20-something that likes to hookup without 8 kids. UPGRADE!

  7. Laffey

    These pics remind me of what’s wrong with America.

    Ed Hardy wannabe t-shirts and hoodies, and chicks clutching cigarettes like they were rosary beads…

  8. Tom K

    Look at that guido in picture 1 with the hoodie. He looks like one of the trashy fucking italians from Long Island, NY.

    That asian didn’t upgrade he just got a slutty young version of his wife, and she is not even hot. Once she has kids that party girl shit will be long forgotten and once again he will have another annoying sloppy bitch for a wife.

  9. hmna

    Ms. Glassman just reeks of class and dignity.

  10. In da butt

    I have a felling this Hailey chick will take it in the ass….from several people.

    She is probably rocking Jon’s world everytime he turns around. That poor sap doesn’t stand a chance. There is no way his lazy ass is keeping up with that.

  11. Tom K

    Exactly #7. I was thinking the same thing!!! America is becoming a bunch of wannabe rock star, wigger, weed smoking clones and trashy whores. Disgusting.

  12. Karl

    Stay classy, San Diego.

  13. Oh yeah, she’s my kinda’ girl!

  14. The Jerk

    That must be cool to take pictures of yourself getting high. Such a kodak moment..

  15. Elisa

    At #6….UPGRADE???? Well, I guess you and I don’t have the same definition for the word upgrade!

    Ha, ha, ha, ha at #8, Tom K, exactly! Same thing, just younger but it ain’t upgrade, that’s for sure!

  16. dirk

    Looks like she’s bogarting the weed in every pic. Plus, what is that group, the hebe wannabe mafia?

  17. Mister Bored

    #11, it’s not “wannabe rockstar, wigger” at all just to be some trashy white chick with an oral fixation. It’s just called being white and classless.

    Which is not too surprising… she seems like she’s the type that wants to do very little in order to get famous.

  18. Courtyardpigeon

    Seriously, I hate wiggers. I don’t get them. Why not act, say, American Indian if you are going to copy another culture? Drown them all. I have many black friends who own their own companies and laugh at these idiots. I’d love to punch those two douche bags in the first photo right in the face.

  19. New Reality Show

    Here is an idea for a new reality show.

    Jon and Hailey plus 8….the 8 being 8 other slutty friends of Hailey’s where they all get together and do drugs and get drunk and have a mad, crazy orgy. Pan over to Jon curled up in the corner sobbing like a baby cause he can’t get it up.

    She may not be the best looking girl out there, she may have been rode hard for the last 5 years of her life but I would still bang that chick until she was retarded. I would hit that till I broke my dick.

    Homely looking or not….you know that girl will be the best fuck you ever had.

  20. britnybitch

    who the fuck is jon gosselin?

  21. havoc

    Gee….I don’t know. You really think she puts out?


  22. I wanna see the video

    pic #6 – her friend is hot

    I wonder if there is a video of these two eating each other out?

  23. Don't Panic

    Is there ever a time where she ISN’T smoking? Guess that explains why she looks like a leathery, busted 40 year old streetwalker.

    She tried to get onto two tv shows, Jon’s a bigger moron than I thought if he doesn’t see what’s going on.

  24. @3 AHAHAHHHAHAH that is exactly what i was thinking!

  25. Just imagine what would happen if she were left alone with the kids. She’d probably try to sale 4 of them just to feed her drug habit.

  26. Where party @?

    Why would you want to be famous from starring in a reality show, sit your ass home if you dont have any hidden talent like a Meryl Strip. Youre only setting yourself up for mockery, the article sound totally logical….

    btw she went 2xtra notch on the hot scale…

  27. rick springfield


  28. Max Planck

    Condom spokesmodel…wouldn’t YOU wear one?

  29. Hello

    I love pic# 5, true friends would always take a picture first before seeing if you still had a face , and the guy that keeps flipping the bird truly classy. I wish my friends were that cool. What a pack of losers. Well at least she got a free trip.
    Hope Jon is using a condom, I would just wrap my whole body in saran wrap, just in case something crawls out of the skank. Go Kate you always had my vote, cause he is one lazy piece of shit.

  30. Hello

    I love pic# 5, true friends would always take a picture first before seeing if you still had a face , and the guy that keeps flipping the bird truly classy. I wish my friends were that cool. What a pack of losers. Well at least she got a free trip.
    Hope Jon is using a condom, I would just wrap my whole body in saran wrap, just in case something crawls out of the skank. Go Kate you always had my vote, cause he is one lazy piece of shit.

  31. Hammertime

    I love party girls…

  32. Inmate #2648927

    These pigs wouldn’t make it at a county fair.

  33. green house

    Damn tree hugger. That plant clearly said ‘no!’.

  34. Now that’ve finally take a good look @ her, She’s the only sub-celeb that manage to add 3syllable to the word fug…


  35. Sotto Cinco

    Rich kid living it up on parent’s hard earned $$$. Typical.

  36. Spud McKenzie

    From classy to trashy

  37. SHE’S THE FUCKING BEST EVER! Jon’s only with her for ass because bitchy cunt Kate only wanted to bitch. Good for him.

  38. Jimboooooooooooo

    Who are these fucking people, and why are they alive? What the fuck with pic #1, god I hate them, whoever they are, stupid looking monkey fuckers.

  39. Maybe she makes Jon feel like a man instead of a pussywhipped douch

  40. Dee

    What a fucking piece of trash. Would you want your kids around someone like that? I hope it’s worth it to him, he keeps it up maybe he’ll loose all visitation. Looser.

  41. Annie Rexia

    Nice gang sign coming from Mac Daddy Liebowitz in the first pick. I wonder if he learned that prepping for his bar mitzvah. What’s up with his douche bag buddy? He’s actually checking himself giving the finger, just to make sure he’s doing it right.

  42. lol

    look how shitty that blunt is rolled, i bet that guy who looks like tommy lee with
    down syndrome rolled it

    3rd pic…..she looks like nicole richie with bells palsy

  43. lolmore

    The first pic is the newest form of birth control… god, its like the evolved backwards

  44. havoc

    LMAO @ #41…


  45. mark

    The Oy Vey Posse!

  46. Jon Gosselin

    You spend 10 years married to Kate and see what kind of madness you descend into…

    Have you even seen my wife’s hair?

  47. crazypants

    WTF is the matter w/ you people – she’s a 20 something year old single girl.

    She SHOULD BE drinking and fucking and partying and getting high, if she wants to!

    Bunch of fucking virgins and nerds the lot of you, if you never blazed up and partied at that age.

    That said – tres dumb to put that shit on Facebook, but you know what, like 90% of everyone on Facebook is an idiot becaase they put all of their private shit online for the world to see.

  48. gag

    i can smell her rotten stinking crotch from here

  49. Slaappy

    Rename the show: “Jon skipped on Kate, hence minus eight”

  50. Do_Freebird

    Can you blame the poor fuck? The Michellin Man would look better than his wife in a bikini.

    He could have picked someone who didn’t look like a burnt out crack whore though.

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