Jon Gosselin sure knows how to pick a winner.

Here is Hailey Glassman’s mugshot photo from four years ago.

Jerry Minger, the communications officer at the Indiana University Police Department, tells Us Weekly that Hailey and five friends were hanging out in a parking lot at 3:18 a.m. on Oct. 2, 2005. A cop spotted the group “passing a pipe back and forth, which is consistent with marijuana.”

Radar reports that the case was eventually settled out of court. She paid fines and court costs, and was placed on probation. Hailey was back in court in April 2007 for illegal consumption of alcohol. The booze charge was dismissed and Hailey paid a small fine and entered a pretrial diversion program for the drug bust.

And since going public with their relationship, Hailey has decided to play the classy girlfriend, but pictures have recently surfaced showing otherwise. Sources inside Hailey’s inner circle tell Hollyscoop that she would often drink, party, and smoke marijuana with just about anyone who would be willing to participate in the fun.