The movie is based on author Jane Green's 2014 New York Times best-selling novel of the same name.. Watch this trailer of Lifetime movie Tempting Fate and tell us if you like this new drama from the network. Based on the New York Times best-selling novel of the same name, “Tempting Fate” follows the story of mother-of-two Gabby (Alyssa Milano) whose picture-perfect marriage to Elliott (Steve Kazee, “Shameless”) is jeopardized when she meets Matt (Zane Holtz, “From Dusk Till Dawn: The Series”), a handsome younger man who seemingly ignites a fire and desire within her. Tempting Fate is a 2019 American made-for-television drama film directed by Kim Raver in her directorial debut and Manu Boyer, starring Alyssa Milano as a married housewife who becomes pregnant with another man's baby. Alyssa Milano discusses her new movie, "Tempting Fate," on Lifetime, codirected by Kim Raver of "Grey's Anatomy," and her thoughts on the topic of abortion in the film. Tempting Fate (2019 Lifetime) Stars: Alyssa Milano, Jessica Harmon, Emilija Barana Watch the movie Listen to the Lifetime Uncorked Podcast here! Synopsis (via Lifetime) Based on the New York Times best-selling novel of the same name, "Tempting Fate" follows the story of mother-of-two Gabby (Alyssa Milano) whose picture-perfect marriage to Elliott (Steve Kazee, "Shameless") is… Tempting Fate Lifetime Movie Trailer. What begins as a business opportunity develops into an emotional affair, leading Gabby to succumb to his unrelenting attention; not foreseeing the life changing consequences. Blog, Drama, Movie Reviews Tagged: 2019, 2020 Lifetime Movies and TV Shows, Drama, TV Movies « Love, Take Two Movie on Hallmark. With Alyssa Milano, Zane Holtz, Steve Kazee, Jessica Harmon. Directed by Manu Boyer, Kim Raver. Gabbys marriage to Elliott is jeopardized when she meets Matt.