Tempting Fate (2019): Summary, Cast, and Where to Watch the Lifetime Drama

Here is a summary, star cast, and availability information for the 2019 TV movie Tempting Fate.

Tempting Fate (2019)
Tempting Fate (2019) movie poster.

Tempting Fate (2019) Summary

Tempting Fate is a made-for-television drama film based on the 2014 novel of the same name by Jane Green.

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The story centers on Gabby Cartwright (Alyssa Milano), a seemingly happily married mother of two teenage daughters. Her life is upended by mounting tension in her marriage to her husband, Elliott (Steve Kazee), particularly due to his decision to get a vasectomy without consulting her, ending her desire for a third child.

During a temporary separation—while Elliott takes their daughters on a trip—Gabby attends a party with a friend and meets Matt Shaw (Zane Holtz), a handsome, younger web developer with a philanthropic side. What begins as a professional working relationship, when Matt hires Gabby as a designer for a local school project, quickly escalates into an intense emotional affair. Despite Gabby’s internal conflict and attempts to maintain boundaries, she eventually succumbs to the attraction.

The affair has life-changing consequences when Gabby discovers she is pregnant. She confesses the truth to Elliott, leading to the devastating collapse of their marriage and a falling out with her older daughter. As Gabby tries to rebuild her life, she attempts to buy out Elliott’s share of their home and reconcile with her family.

The film follows the complexities of the aftermath, culminating in the birth of her son and the difficult process of all parties—Gabby, Elliott, and Matt—navigating the new reality of co-parenting and co-existence.

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Star Cast

RoleActor
Gabby CartwrightAlyssa Milano
Elliott CartwrightSteve Kazee
Matt ShawZane Holtz
ClairJessica Harmon
Olivia CartwrightEmilija Baranac
Alana CartwrightBeatrice Kitsos
TrishLucia Walters

Directors: Manu Boyer and Kim Raver

Availability

Tempting Fate (2019) is a Lifetime film and is often available to watch on platforms that carry Lifetime content. You can typically find it available for:

  • Streaming/Subscription: It has been available on services like Hoopla and Plex.
  • Rental/Purchase: It is commonly available to rent or buy on digital video stores such as Amazon Prime Video, Apple TV, Google Play Movies & TV, and Vudu (Fandango At Home).

Availability can change, so it’s always best to check the current listings on your preferred platform.

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