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.

She restores furniture as a hobby, while her husband Elliott (Steve Kazee) works as a doctor to provide for the family.

Unbeknownst to many, her marriage is currently going through a rough patch: Gabby desperately wants to have a third kid, but Elliott is unwilling and underwent a vasectomy without consulting his wife.

In order to reduce tensions inside the house, Elliott takes the kids on a weekend trip to Vermont while she stays at home.

Even though Gabby upfront tells him about her marriage, they hit it off, and Matt invites her to join a business meeting the next day.

Seeing her life fall apart, Gabby tries to make amends, and puts all of her energy into her furniture restoration to earn enough money to buy the house from Elliott.

Despite her attempts to save their marriage, Elliott cannot forgive her and starts to date Trish (Lucia Walters), an acquaintance of Gabby.

In June 2018, it was announced that three Jane Green novels would be adapted for the small screen, with Kim Raver as the director for and Alyssa Milano as the leading actress in Tempting Fate.

[2] Milano signed on for similar reasons: "Having a movie that combines the sensationalized idea of infidelity but still giving it something that is rounded and has depth and nuance.