The Thomas Crown Affair (1999)

Thomas Crown (Pierce Brosnan) is a bored billionaire who steals a painting from the Metropolitan Museum of Art for fun. Catherine Banning (Rene Russo), an insurance investigator, is hired to catch him. She decides to get close to him, and he lets her.

What it shows about dating

Crown is the picture of calm confidence. He is never in a hurry, never chases, and treats Catherine as an equal who has to earn his attention too. Their meetings turn into a game of teasing, challenge and withdrawal, with a chess scene as the best-known example. Both are used to being in control, which is exactly why the attraction works: neither is impressed easily.

What you can learn

• Be hard to read, not hard to like. Crown stays amused and relaxed, which makes her curious instead of defensive.
• Match her level. A woman with her own power wants a partner who enjoys the challenge instead of folding.
• Trust is the real test. The film is fair about the limits of games: tension builds attraction, but it doesn’t build trust.

For the dynamic at work here, see DHV.