Tempting Fate (2019 Lifetime)

Tempting Fate (2019 Lifetime)

Cast: Alyssa Milano, Jessica Harmon, Emilija Barana

Listen to the Lifetime Uncorked Podcast here!

Watch & Stream the movie here! #Ad

Please buy me a coffee (or glass of 🍷 ) Support Lifetime Uncorked by leaving a $3 tip.

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 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. What begins as a business opportunity soon develops into an emotional affair leading Gabby to eventually succumb to Matt’s unrelenting attraction and attention, never foreseeing the life-changing consequences that lie ahead.


The title card plays with moaning underneath, and I know we are in for a sultry good time or maybe not. Alyssa Milano (Character name is Gabby, but she is too big of a star to not be referred to by name.), and her husband, Elliot, are having sexy bed time. He ruins the mood. Alyssa yells at her husband for getting a vasectomy without even telling her. They have two teen daughters, who love to TEXT and take PHOTOS.

Clair, Alyssa Milano’s (friend? Neighbor?) takes her to a ridiculous party where 40-year-old women are dancing in brunch dresses in the middle of the day. WTF?!!? Alyssa Milano orders a dirty martini at the bar and reads Jane Eyre on the kindle app on her iPhone… A handsome young man named Matt interrupts her reading time to tell her that he loves the book she is reading. He is at the party with a business associate and is 32. He compliments Alyssa Milano, and she is very flattered but tells him she has kids, is married, and has a white picket fence. While Alyssa Milano takes a call, Matt looks her up online and learns she refinishes furniture. He invites her to check out a project he is working on in the city. (He does social media, so I’m not sure how that fits in with the furniture.)

Turns out, Matt is wealthy and owns a Facebook type of social media called four4sitet. He grew up in the foster care system and is all about traveling the world and giving back. Alyssa Milano goes to visit a school he is building, and Matt offers a job working on the project

Clair and her husband get pregnant, which kicks off a fight with Alyssa Milano and Elliott. She is hurt and betrayed by him getting a vasectomy and not telling her. He apologizes, and she tells him to prove it and reverse the procedure. He refuses, and their relationship is seriously on the rocks.

Matt and Alyssa Milano are texting now. (They do that thing with the text when it pops up on the screen, instead of filming the phone. I appreciate that.) She agrees to work on the project with him, and they correspond for months. We get a quick montage where she sends him leaves when it is fall, he sends her sand from Malibu, they send selfies, and now Clair is 9 months pregnant. The flirting via text is getting pretty intense, and Alyssa Milano is having doubts. (I mean he texts her when she is in YOGA!!!)

When Matt is in town, Alyssa Milano agrees to go to dinner with him and some work sociates. (She even buys a new dress, that her husband doesn’t even notice.) Alyssa Milano is surprised when she gets to dinner that it is only, Matt. She shuts him down for flirting with her in person when he knows that he can’t have her. She doesn’t want to have an affair and tells him that she just wants to be friends. They toast to that. He later texts: “Thanks for the fun night… friend.” Then the texting is out of control!!!!!!!!!!! 

More time goes by, and Alyssa Milano is home alone for the weekend when Matt pops by “for work.” The woman is literally vegging out, eating pasta. (I love her. Is she me?) Alyssa Milano pulls herself together, and he is impressed with her woodworking shop. He is more impressed with her “woodworking shop” if you know what I’m saying. They totally hook up, and it is steamy! (and actually really well shot.)

Alyssa Milano is upset with herself for what she has done and goes to tell Matt that it can’t happen again. He tells her that he likes her, but it was just one night, and everything is going to be alright. (FAMOUS LAST WORDS, MATT!) 

Alyssa Milano throws herself back into yoga and quality time with her family. The tactic works except for her short temper with her daughters and, oh, yeah… she is pregnant. Alyssa Milano asks the doctor what percentage it could be her husband’s who had a vasectomy. 0.5%

Clair tells Alyssa Milano to get an abortion and save her marriage. Alyssa Milano has wanted to have this baby for so long and could never have an abortion. Alyssa Milano comes clean with Elliott about the affair. He, of course, freaks out on her and she tells him that they can work through this. They can finally have the baby she always wanted and asks him to pretend that it is his baby. He storms out of the house, and Alyssa Milano screams after him. “ELLIOT”

Next, Alyssa Milano and Elliott have to tell their daughters the truth. They can’t work it out, and she had an affair. The daughters are like, “Ummm, we are kids. Why are you roping up into your drama?” Elliott takes one daughter, and Alyssa Milano takes the other. The family is shattered. Alyssa Milano is trying to put back the pieces.Alyssa Milano’s sister comes over with chocolate cake and tells her that she has to move on the best that she can.

Alyssa Milano takes her advice and goes to see Matt. She nonchalantly asks him if he wants kids, and he straight up says no. Hahaha. 

Now alone and pregnant AF, Alyssa Milano meets up with Elliott to talk about selling the house. She is surprised he wants to sell the house and that he wants to divorce her. He tells her that she has left him no other choice. Her friend Clair is also giving up on her and is rude to her in yoga. Olivia, her daughter, hates her. All Alyssa Milano has is her deadbeat sister and her yet to be born baby. 

With lots of time to think, Alyssa Milano tells Elliott that she will buy out his share of the house. Her sister is obsessed with yard sales and arranges a pop-up furniture store. Olivia and the other daughter show up to help with the pop-up store, and we get a montage of them doing just that. Alyssa Milano sits in a rocking chair while everyone else does the work. 

It is Christmas, and Alyssa Milano invites Elliott to spend Christmas Eve and Christmas day with her and the daughters. While shopping, Alyssa Milano bumps into Matt, who realizes that she is super pregnant. Alyssa Milano tells Matt that she should have told him… Matt is upset that she didn’t tell him sooner. Alyssa Milano is not a likable character in this movie, I’m sorry.

On Christmas morning, after learning that Elliott is dating someone else, Alyssa Milano goes into labor. Elliott is there to hold her hand as she gives birth. She says his name, and Elliott is shocked that the kid is going to his last name and runs off. Alyssa Milano tells the baby that she is going to love him so much. 

Alyssa Milano sends a text a pic of the baby to Matt, which is fitting because MOST of their relationship was via text. He doesn’t respond, but he does eventually show up unannounced to meet his son. Alyssa Milano’s daughter meets Matt, too, and they are super annoyed that he is there. Olivia and Alyssa Milano talk and come to understand that this is their life now, and they need to move through it. Of course, Elliott shows up to try to get Alyssa Milano back and see her with Matt.

At prenatal yoga, Alyssa Milano runs into Clare and Elliott’s new girlfriend. It is awkward!!!!! Elliott’s girlfriend tells Alyssa Milano that she broke up with him and tells him to go get her man. They were meant to be together. They kiss on the cheek, and Alyssa Milano runs off, pushing a stroller and goes to Elliott’s office. Alyssa Milano tells him that she wants to be with him, and she is sorry. In the middle of the office, Elliott apologizes, too, and they get back together while inspirational music swells. The family may not be just like the beginning of the movie, with the addition of the baby, Matt, and his model girlfriend. They are making it work, and Alyssa Milano is very happy.

Side Note

Minority Report: Trish (Elliott’s girlfriend.) Clair’s husband and the doctor.

I’m happy Alyssa Milano is back on Lifetime. Her last TV movie was in 2016

Not sure how I feel about Lifetime’s new genre shift? What do you think?

Don’t forget to listen to the Lifetime Uncorked Podcast available on iTunes, Stitcher, Spotify, or wherever you listen to podcasts!

 Donate to keep the blog and podcast going 😊

Overall rating

❤️❤️❤️ (3 Hearts)

🍷🍷🍷🍷 (4 glasses of wine required)

*Photo Credit: © 2019 Lifetime


  1. I really liked this one & would have rated it 4 hearts. I actually put the book this was based on on my list of books to read. Was that one chick supposed to be her sister? lol I never knew who she was, just that she popped up occasionally to make Alyssa Milano feel better about herself.

  2. I think it was one of the most depressing movies I have ever seen. A beautiful woman a beautiful family she doesn’t even use protection he doesn’t use protection. He’s a predator. A handsome One but still a predator. Disgusting movie. Made I think, to make Alyssa hey beautiful woman, a little older, and a young man can’t keep his hands off her. I dream of every aging actress.

Share your thoughts about this movie

This site uses Akismet to reduce spam. Learn how your comment data is processed.