Best friends since they were kids, Jake Schram (Ben Stiller) and Brian Kilkenny Finn (Edward Norton), are single, successful, handsome, and confident young men living on New York’s Upper West Side. When Anna Reilly (Jenna Elfman), once their childhood friend and now grown into a beautiful corporate executive, returns to the city, she reenters Jake and Brian’s lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle is created because Brian happens to be a Roman Catholic priest and Jake is a rabbi.