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  1. About this movie. arrow_forward. A divorced mother of two, while on vacation on the brink of her 40th birthday, enters into an unexpected romance with a much younger man and learns that life can...

  2. Flirting With Forty. DRAMA. Jackie (Heather Locklear, TV's "Spin City") is a recently divorced mother of two vacationing alone in Hawaii for her 40th birthday. Against her better judgment, she allows the hunky, much younger, resident surf instructor (Robert Buckley, TV's "Lipstick Jungle") to sweep her off her feet.

  3. Flirting With Forty (2008) - Turner Classic Movies. 2008. Overview. Synopsis. Credits. Film Details. Notes. Brief Synopsis. Read More. Divorced with two kids, Jackie is facing her fortieth birthday, and she is depressed. Her friend decides that they should go to Hawaii to celebrate but backs out once they're at the airport.

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