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Struggling photographer Pia (Simone Ashley) receives a prediction: true love and career success await her in the next five dates she goes on. With her sister's wedding looming and family playing matchmaker, her ex (Hero Fiennes Tiffin) reappears, throwing both her love and professional life into chaos.
New York sportswriter Mack (Gina Rodriguez) has spent years devising successful hook-up “plays” with best friend Adam (Damon Wayans Jr.) and their crew, but when she unexpectedly falls head-over-heels for one of her targets (Tom Ellis), they all must learn what it takes to go from simply scoring to playing for keeps.