Jon Gosselin Spotted Grabbing Drinks With Old Flame Hailey Glassman
![Jon Gosselin Hailey Glassman Together New York](https://media.radaronline.com/brand-img/zfbC95v5h/480x251/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 480w, https://media.radaronline.com/brand-img/zfbC95v5h/640x335/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 640w, https://media.radaronline.com/brand-img/zfbC95v5h/768x402/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 768w, https://media.radaronline.com/brand-img/zfbC95v5h/1024x536/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 1024w, https://media.radaronline.com/brand-img/zfbC95v5h/1280x670/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 1280w, https://media.radaronline.com/brand-img/zfbC95v5h/1440x753/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 1440w, https://media.radaronline.com/brand-img/zfbC95v5h/1600x837/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 1600w, https://media.radaronline.com/brand-img/zfbC95v5h/2160x1130/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg?position=top 2160w)
Mar. 10 2017, Updated 7:53 p.m. ET
Are Hailey Glassman and Jon Gosselin back together? Eight clicks tells the story.
![Jon Gosselin Hailey Glassman Together New York](https://media.radaronline.com/brand-img/KcgUr5I_v/480x300/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 480w, https://media.radaronline.com/brand-img/KcgUr5I_v/640x400/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 640w, https://media.radaronline.com/brand-img/KcgUr5I_v/768x480/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 768w, https://media.radaronline.com/brand-img/KcgUr5I_v/1024x640/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 1024w, https://media.radaronline.com/brand-img/KcgUr5I_v/1280x800/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 1280w, https://media.radaronline.com/brand-img/KcgUr5I_v/1440x900/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 1440w, https://media.radaronline.com/brand-img/KcgUr5I_v/1600x1000/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 1600w, https://media.radaronline.com/brand-img/KcgUr5I_v/2160x1350/2015/10/jon-gosselin-hailey-glassman-together-new-york-2-PP.jpg 2160w)
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/txvYvQzDw/332x499/2015/10/jon-gosselin-hailey-glassman-together-new-york-02.jpg 332w)
The Jon & Kate Plus 8 dad, 38, and ex-gal pal Hailey Glassman, 28, were spotted in New York recently, clinking drinks on a tiny table for two at a sidewalk café.
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/xDKGa-hfG/332x499/2015/10/jon-gosselin-hailey-glassman-together-new-york-03.jpg 332w)
"Jon and Hailey were celebrating signing a contract, and they were in a very good mood," an insider told RadarOnline.com about their outing.
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/PN3t2_axC/480x320/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 480w, https://media.radaronline.com/brand-img/PN3t2_axC/640x426/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 640w, https://media.radaronline.com/brand-img/PN3t2_axC/768x511/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 768w, https://media.radaronline.com/brand-img/PN3t2_axC/1024x681/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 1024w, https://media.radaronline.com/brand-img/PN3t2_axC/1280x852/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 1280w, https://media.radaronline.com/brand-img/PN3t2_axC/1440x958/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 1440w, https://media.radaronline.com/brand-img/PN3t2_axC/1600x1064/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 1600w, https://media.radaronline.com/brand-img/PN3t2_axC/2160x1437/2015/10/jon-gosselin-hailey-glassman-together-new-york-04.jpg 2160w)
A PR maven now, Glassman was fresh out of college when she first connected with Jon and he was married to Kate Gosselin and starring with their eight children on the hit show.
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/MhU7-Yh_1/480x320/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 480w, https://media.radaronline.com/brand-img/MhU7-Yh_1/640x426/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 640w, https://media.radaronline.com/brand-img/MhU7-Yh_1/768x511/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 768w, https://media.radaronline.com/brand-img/MhU7-Yh_1/1024x681/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 1024w, https://media.radaronline.com/brand-img/MhU7-Yh_1/1280x852/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 1280w, https://media.radaronline.com/brand-img/MhU7-Yh_1/1440x958/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 1440w, https://media.radaronline.com/brand-img/MhU7-Yh_1/1600x1064/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 1600w, https://media.radaronline.com/brand-img/MhU7-Yh_1/2160x1437/2015/10/jon-gosselin-hailey-glassman-together-new-york-05.jpg 2160w)
Glassman traveled the world by his side, but after a whirlwind romance, Gosselin announced their split on Halloween in 2009.
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/l7ToyUZ0p/480x456/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 480w, https://media.radaronline.com/brand-img/l7ToyUZ0p/640x608/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 640w, https://media.radaronline.com/brand-img/l7ToyUZ0p/768x730/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 768w, https://media.radaronline.com/brand-img/l7ToyUZ0p/1024x973/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 1024w, https://media.radaronline.com/brand-img/l7ToyUZ0p/1280x1216/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 1280w, https://media.radaronline.com/brand-img/l7ToyUZ0p/1440x1368/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 1440w, https://media.radaronline.com/brand-img/l7ToyUZ0p/1600x1520/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 1600w, https://media.radaronline.com/brand-img/l7ToyUZ0p/2160x2052/2015/10/jon-gosselin-hailey-glassman-together-new-york-06.jpg 2160w)
Six years later, it seems like any lingering bitterness over the breakup is long forgotten!
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/oRfakNHkm/480x320/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 480w, https://media.radaronline.com/brand-img/oRfakNHkm/640x426/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 640w, https://media.radaronline.com/brand-img/oRfakNHkm/768x511/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 768w, https://media.radaronline.com/brand-img/oRfakNHkm/1024x681/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 1024w, https://media.radaronline.com/brand-img/oRfakNHkm/1280x852/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 1280w, https://media.radaronline.com/brand-img/oRfakNHkm/1440x958/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 1440w, https://media.radaronline.com/brand-img/oRfakNHkm/1600x1064/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 1600w, https://media.radaronline.com/brand-img/oRfakNHkm/2160x1437/2015/10/jon-gosselin-hailey-glassman-together-new-york-07.jpg 2160w)
While Glassman's career as a publicist flourished, Kate Gosselin's ex hadn't fared as well, so far. "Jon has really hit rock bottom," a source told RadarOnline.com, noting that he once earned $22,500 an episode on the TLC show, but now is just "waiting tables at a pub!" He also DJs at local bars in Pennsylvania.
EXCLUSIVE: INF – Kate Gosselin and her kids visit Toys “R” Us
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/WWL7LvgyA/426x500/2015/10/jon-gosselin-hailey-glassman-together-new-york-08.jpg 426w)
But that's where Glassman comes in. According to the insider, Jon enlisted Glassman for her industry expertise and she's helping him to plot his big comeback. "Jon is trying to turn things around with Hailey's help, and get a little good press in the process!" the insider explained. What do you think about Hailey and Jon's new relationship?
GOSSELIN
![Jon Gosselin Hailey Glamssman Together New York](https://media.radaronline.com/brand-img/2a80iqbHK/480x360/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 480w, https://media.radaronline.com/brand-img/2a80iqbHK/640x480/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 640w, https://media.radaronline.com/brand-img/2a80iqbHK/768x576/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 768w, https://media.radaronline.com/brand-img/2a80iqbHK/1024x768/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 1024w, https://media.radaronline.com/brand-img/2a80iqbHK/1280x960/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 1280w, https://media.radaronline.com/brand-img/2a80iqbHK/1440x1080/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 1440w, https://media.radaronline.com/brand-img/2a80iqbHK/1600x1200/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 1600w, https://media.radaronline.com/brand-img/2a80iqbHK/2160x1620/2015/10/jon-gosselin-hailey-glassman-together-new-york-01.jpg 2160w)
Reality TV dad Jon Gosselin reconnected with the feisty flame whose father performed his ex-wife’s boob job and RadarOnline.com has new exclusive details inside their romantic date.