Kristin Cavallari and Jay Cutler's Windy City Reunion

Kristin Cavallari and Jay Cutler's Windy City Reunion
Charlie Luciano/StarTraks

11/15/2011 AT 05:55 AM EST

She must be his lucky charm! Before the Chicago Bears's big win on Sunday, quarterback Jay Cutler dined with his on-again girlfriend, Kristin Cavallari, at Joe's Stone Crab in Chicago. The pair ordered up fried oysters, stone crab, turbot and Parmesan halibut, and Cutler "appeared more happy and relaxed than he's been in a long time," a source tells PEOPLE. – Jennifer Garcia



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