Sam's Cafe Romances Series by Ashavan Doyon

Russell Pine goes to the café every morning to enjoy his time chatting with Sam Tesh, the café owner, a friend made over the past twenty years. So when Sam asks a favor, Russ reluctantly agrees to play in a chess tournament. But the contest isn’t the real challenge: Russ finds himself the focus of a secret courtship in words and pictures left for him to discover each morning, leading him to the question: In a café full of young and beautiful minds, who is looking at the graying chessmaster?