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Jon Gosselin and Hailey Glassman broke up in late November 2009. However, this was long before the relationship broke down under the strain of financial pressure and… Jon Gosselin and Hailey Glassman dated in mid-2009 - but have moved on to other relationships since that time.

Various Wikianswerers opinions: * Hailey Glassman, soon to be Hailey Gosselin, is telling former friend, Kate Gosselin that Jon never loved her. See related links for photos from Jon Gosselin's trip with Hailey Glassmen to France to visit with Ed Hardy designer Christian Audigier.

Most recently, Jon was said to have proposed to Hailey during their getaway in St. Neither of them has acknowledged the report though.

Last we checked in on him Jon Gosselin was delighting in Kate Gosselin getting dumped by millionaire Jeff Prescott.

Obviously, Jon has had his share of failed relationships in the years since his marriage ended, but now it looks like he might be giving one of them a second chance.

During their outing both Jon and Hailey seemed enjoying each other's company very much.

At one point, Hailey even grabbed a flower and put it behind Jon's ear. Later that day, the lovers lunched at Rocco's Restaurant and were spotted leaving with pizza boxes and doggy bags.

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