Gosselin and Glassman Play Kissy Face 10/18/2009 3:09 AM PT Jon Gosselin and his girlfriend Hailey Glassman arrived to a dinner date at The Oak Room in New York in a horse and carriage. That loud explosion you just heard would be Kate Gosselin's head exploding. More Jon & Kate Jon Gosselin Googles Lawsuits ... Not BabiesTLC to Jon -- Pants on Fire!TLC to Jon Gosselin -- Sue You!!! Share on Facebook Share on X Hailey Glassman Jon Gosselin Jon & Kate Ride Me Paparazzi Photo