Flirting with Forty (2008)

Jackie Laurens (Heather Locklear) is a recently divorced, 40-year-old and mother of two pre-teen kids who takes a vacation alone to Hawaii where, against her better judgment, she meets and hooks up with a hunky, much younger resident surf instructor named Kyle Hamilton (Robert Buckley). But what began as a one-night stand turns into love as when her vacation is done, she flies to Hawaii every chance she gets to meet with her latest love interest, which soon gets disapproval from her ex-husband, her teenage kids, and even her close friends. As time and the pressure from everyone around her to break it off with Kyle pushes Jackie to her breaking point, it will only take her beau Kyle to teach her how to cope before life passes her by.