Hailey Glassman Pictures: "The Biggest Ditz"

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Jon Gosselin’s new girlfriend, Hailey Glassman, seems like the type who would be a classy, upstanding role model as a stepmom to his eight small children.

Well, if you exclude the mug shot. And pretty much every other photo taken of her before this past weekend, when she actually looked sober for a change.

As more details of the 22-year-old's background come to light, we are beginning to learn what makes Hailey Glassman tick. Her interests include working out, being a stylist, fashion, art, music and looking old and haggard.

Just kidding about the last part. Okay, not really. Here's the aspiring kids' fashion line designer with a couple of dudes who are clearly thinking 2-on-1 ...

Hailey Glassman is “the biggest ditz” according to a high school classmate. Her AIM screen name? Goldeloks18, complete with an icon of a cat smoking a joint.

Her Facebook page also says she is "In a Relationship" as of May 1. This date is assumed to be when Jon Gosselin started tapping that - at least not secretly.

But does Jon have reason to worry about Hailey Glassman's faithfulness? One of her Facebook groups is "Not a fan of fat people." Better hit the gym, J!

Other highly intelligent declarations of hers: "Hi, I'm _____ and I'm sooooo f*%king addicted to Guitar Hero" and "FIGHTING TO LEGALIZE MARIJUANA!"

What a catch she is.

Click to enlarge more Hailey Glassman pictures below to really get to know Jon Gosselin's girlfriend, the personification of demure beauty and class:

Hailey Glassman Mug Shot
Jon Gosselin, Hailey Glassman
Hailey Glassman Photo

Hailey, what goes around comes back around. You're 24 now, but by 34:
1) You will no longer, EVEN, speak to Jon
2) You will want a loyal partner of your own (we'll call him Bob)
3) You will not be able to comprehend how the female, Bob's giving time to, sees nothing wrong or no disrespect on her part. How she can watch him lie to you. She even, creatively, helps him at times, yet believe what he tells her is the truth.
4) You will have become more morally mature(hopefully)
5) You will want a successful business
Today, you are blocking your blessings for years to come.
Jon, it's clear you're a SMALL guy & that, in itself, can inspire insecurity. Bumps, rashes, & discharge will NOT serve to make it appear larger.
Educate yourself, 4 the sake of 8 lil 1's that look just like U.


Hello what are u thinking jon kate is a good women! You need to stop talking crap about her n respect her. She is the mother of your kids! No one will ever take her place so u need to at least give her that respect. Yes she may have her bad but u did to! Now u have this new girl who doesnt care about anything n about your kids! Hellooooo is any one home! That should be a red flag that she isn't the one for those kids! You need to walk away n find some one else. Unless u like sloppy seconds! I think twice!!!!


Obviously he dosen't care about the well being of his children if he is around her. with pot and pipes. thats not really something you should be open about...i think kate should get full custody and he shouldn't be able to see his children unless kate is around.


I thought they needed counseling but now it is way passed that it is time for Kate to move on to a man that we be behind her in the good and the bad times, that is what marriage is about. Jon is the sell out. Grow up Jon!!!!


Hes a midget loser, Kate and those kids are the only thing that made him a decent human being. Now he is a HUGE waste of space. Everyone knows Kate is controlling .... Someone had to be. You cant maintain 10 people and not have control. I pray for her, she has alot on her plate and I hope she finds the strength to get through it, as for him .... I hope he gets a painful STD!!


Jon Gosselin is an idiot. As he said in the last episode he's excited about this new chapter in his life. What about your kids lives? If Kate was as bad as you have led others on to think she is why didn't you just tell her how you felt and then try counseling? Women can change, but it helps if you open your mouth up to us? You should have put Kate in her place to begin with and let her know you weren't going to take the way she was treating you and then try to work on the marriage. But, no, you just give up on her and your kids cause your too young bull..... Grow up man your 32 yrs. old, not 18. Oh, and Hailey, great role model. If I was Kate, she wouldn't be anywhere near my kids.


She's a skank and he's going through a midlife crisis!


She's the kind of girl I made fun of in high school for opening her legs to every man-slut (lol) that would have her. Hello?


Skank. Yes.... I said, "SKANK"


Alright Jon!!!! Total good upgrade!!! Can't wait until the taboilts show when he takes her to meet his 8 kids! Too late for you Kate!!!! See-ya!


Hailey Glassman Biography

Hailey Glassman Photo
Hailey Glassman became Jon Gosselin's new plaything after he divorced wife Kate in mid-2009. Prior to Hailey Glassman, Jon was doing... More »
Nyack, New York
Full Name
Hailey Glassman