Though we’ve seen her holding hands and smoking cigarettes with Jon Gosselin in France, Hailey Glassmanis still pretty mysterious to us. Slowly but surely, her past is coming to life. has a mugshot and glimpse into Glassman’s criminal past.  And while she isn’t a murderer, she’s had a couple run-ins with Johnny Law.

2005: Glassman is arrested at Indiana University for possession of marijuana. She was outside smoking with some of her friends when a cop spotted them and arrested her.  Her case was settled out of court.


2007: Glassman was back in court for illegal consumption of alcohol.  I’m not sure how that went down but it was also thrown out.  So she hasn’t served time or anything but she still seems to find herself getting into legal trouble every couple years. We’ll see if 2009 brings her anything new?

See, this totally plays into my prediction that Jon is trying to change his image from wholesome television dad.  He’s attempting to make himself into a tougher, harder person.  Dating a girl with a arrest record, smoking cigarettes in public.  He just needs some hardcore tattoos and he’s on his way!

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