Hailey Glassman: Bong Hits

Hailey Glassman: Bong Hits

Jon Gosselin's new girlfriend and possible fiancee Hailey Glassman hits the bong in a picture obtained by Inside Edition. Man, she is so hot. Definite stepmom material.
Rating: 4.0 / 5.0
A Hailey Glassman Photo

A Hailey Glassman Photo

Hailey Glassman lies on her back, post-bong hit. Where is Blake Powers when you need him.
Rating: 3.7 / 5.0
Hailey Glassman: No Pants!

Hailey Glassman: No Pants!

Hailey Glassman, Jon Gosselin's party animal girlfriend, gets rid of her pesky pants. Those things just get in the way of so much fun when you're Hailey Glassman.
Rating: 3.4 / 5.0
Hailey Glassman and Jon Gosselin

Hailey Glassman and Jon Gosselin

Hailey Glassman and Jon Gosselin make such a sexy couple. Seriously. The heat from them radiates from Pennsylvania all over the U.S.
Rating: 2.9 / 5.0
Boxing Ref

Boxing Ref

Hailey Glassman reffed some girl-on-girl celebrity boxing recently. We could not make that up.
Rating: 2.9 / 5.0
Jon Gosselin, Hailey Glassman

Jon Gosselin, Hailey Glassman

This photo of Jon Gosselin and Hailey Glassman shows the lovebirds in St. Tropez, happy as clams. Or happy as a newly-single father of eight and 22-year-old party girl mistress with an arrest record, at least.
Rating: 2.9 / 5.0
Hailey Kissing Jon

Hailey Kissing Jon

Hailey Glassman and Jon Gosselin go at it in full view of the paparazzi. Well, you have to give them credit for being good sports about the attention they're getting at least.
Rating: 2.8 / 5.0
Jon Gosselin, Hailey Glassman Picture

Jon Gosselin, Hailey Glassman Picture

Jon Gosselin and Hailey Glassman, seen here August 6, 2009, are still an item, according to both of them. They were tracked down by a celeb gossip site who got them to confirm as much.
Rating: 2.6 / 5.0
Jon Gosselin, Hailey Glassman Pic

Jon Gosselin, Hailey Glassman Pic

Jon Gosselin and Hailey Glassman kiss in Pennsylvania. We hope the eight kids get to know and love their new mommy like we are.
Rating: 2.5 / 5.0
Jon Gosselin PDA

Jon Gosselin PDA

Jon Gosselin lays a nice kiss on Hailey Glassman. They've been dating since ... oh, the second he filed for divorce from Kate Gosselin. She is his ex-wife's polar opposite, for better or worse.
Rating: 2.4 / 5.0
Hailey Glassman, Jon Gosselin Pic

Hailey Glassman, Jon Gosselin Pic

Hailey Glassman and Jon Gosselin make the sexiest couple ever. Well, it probably feels like it to him, having been married to that crazy chick for 10 years.
Rating: 2.3 / 5.0
Make-Out Session

Make-Out Session

Hailey Glassman and Jon Gosselin make out in a friend's car. This is just like high school for Jon, who is in prime mid-life crisis mode.
Rating: 2.2 / 5.0

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 »
Born
Birthplace
Nyack, New York
Full Name
Hailey Glassman