Worn by: Matthew McConaughey as Benjamin Barry
Reference: TAG Heuer Monaco
Brand: TAG Heuer
Advertising executive Benjamin Barry makes a high-stakes bet with his boss: make any woman fall in love with him in ten days to win a prestigious diamond campaign. Meanwhile, Composure magazine writer Andie Anderson agrees to write a "How to Lose a Guy in 10 Days" article by deliberately driving away a boyfriend using classic relationship mistakes—inspired by her friend Michelle's recent breakup. Ben's competitive coworkers secretly choose Andie as his target, setting up the collision. Neither reveals their true agenda as Andie employs every annoying girlfriend tactic while Ben endures her behavior to win his bet. Despite the deception, genuine feelings emerge. The classic Tag Heuer Monaco suits Ben's confident advertising executive persona—a ladies' man whose professional success depends on understanding desire and romance.