The Thomas Crown Affair (1999) on Netflix

Competitive New York mergers and acquisitions king Thomas Crown steals a Monet for the challenge only to be fingered as the thief within two days by insurance investigator Catherine Banning who's smart, driven, and alone. Ostensibly she works with the police but in truth she runs her own show playing cat and mouse with Crown. Soon it's a romance: a black and white ball, a glider flight, two days in Martinique. Back in Manhattan, she thinks she has reason to be jealous, so when he suggests they go off together, she hesitates. He may have more tricks up his sleeve and, as his psychiatrist has asked him, what would it take for him to trust a woman and, in turn, be trusted?