Flirting with Forty is a 2008 American romantic comedy-drama television film directed by Mikael Salomon from a screenplay by Julia Dahl, based on the novel with the same name by Jane Porter.

Starring Heather Locklear and Robert Buckley, the film premiered on Lifetime on December 6, 2008.

[1] The film focuses on Jackie (Locklear), a divorced mother who travels to Hawaii for her 40th birthday and meets a young surf instructor named Kyle (Buckley).

[1][2] Jackie Laurens is a recently divorced, 40-year-old and mother of a young son and daughter who takes a vacation alone to Hawaii where, against her better judgment, she meets and hooks up with hunky, 27-year-old resident surf instructor Kyle Hamilton.

However, what began as a one-night stand turns into love, with Jackie flying to Hawaii every chance she has to meet with her latest love interest, which is soon met with disapproval from her ex-husband, her children, and even her close friends.