Lucky Jack O’Brien! The veteran Broadway director had quite the stunning date on his arm—the spectacular Katie Holmes—for the Broadway Dreams Foundation Champagne and Caroling Gala on December 10 in New York City. The mega-famous movie star looked positively pleased to be beside her Dead Accounts director at the gala event, where they shared a table and enjoyed a classy evening at swanky NYC restaurant Celsius. Holmes looked ravishing in a strapless purple gown, while O’Brien was downright dashing with his colorful bowtie. Get a great look at this talented twosome!