If you’re in the middle of a divorce or about to start on one, you’re well aware of the roller coaster ride you signed on for, or your spouse signed you on for, and now you’re along for the ride whether you wanted to be on it or not. Roller coasters, along with divorce, can be petrifying, especially if you didn’t have time to prepare, financially, mentally, or otherwise. If you have kids riding along with you, the experience can be that much more nerve-wracking.
When I was going through my divorce, my days were busy, which was great because I stayed focused on moving forward. I was at a new legal job while caring for my four school-aged kids, who I also homeschooled. I didn’t have time to think.
At night, after the kids went to bed, it was a different story. I often plopped myself down on the couch, not yet ready for bed but exhausted. I needed to unwind, and I found a great way to do that was to grab a glass of wine and a bowl of popcorn and watch movies. Given what I was going through, a lot of those movies were about divorce.
But why watch movies about divorce when I was looking for an escape? Easy. The characters in the films were my people. They were going through a lot of what I was, and I could identify. As they learned, I learned, most notably about how I wanted my divorce and — my life after — to be. Here are a few of my absolute favorites.
1. The War of the Roses
A drama and a dark comedy, this movie is about the Roses, Barbara (Kathleen Turner) and Oliver (Michael Douglas), who have separated. Still, each does not want to leave their house, so hijinks ensue as they try to force each other to go, all the while divorce lawyer Gavin D’Amato (Danny DeVito) is watching. It’s a lesson in what not to do.
2. Waiting to Exhale
This film is a romantic comedy and what I would call the “quintessential chick flick.” It follows friends Vannah (Whitney Houston), Bernie (Angela Bassett), Glo (Loretta Devine), and Robin (Lela Rochon), as they talk through their mistreatment and being cheated on by not-so-good lovers, holding their breath waiting for the perfect man. Even if you haven’t watched the film, you may still recall the image of Angela Bassett lighting her husband’s clothes and car on fire. Not an example to follow but a crazy sight nonetheless.
3. Kramer vs. Kramer
A late seventies classic, this movie is timeless. Dustin Hoffman plays workaholic Ted Kramer who is engaged in a nasty divorce and custody battle with his wife, Joanna (Meryl Streep). Ted gets a hard lesson on what’s important in life, re-evaluating his priorities and moving his son to the top of the list. Dustin Hoffman’s highly acclaimed performance will have you crying, so bring the tissues.
Another tearjerker. Based on Cheryl Strayed’s autobiography, Reese Witherspoon depicts the months following the author’s decision to start a new life and embark upon a thousand-mile hike on the Pacific Crest trail after a tragic past that has now culminated in a divorce. With lots of introspection to offer, the film presents an intense character study and poses many interesting philosophical questions you would expect on a journey toward self-improvement and empowerment.
5. Under the Tuscan Sun
In this romantic comedy, a 35-year-old book editor from San Francisco, played by Diane Lane, goes to Tuscany after her divorce. There, she decides to buy a rundown countryside villa. In over her head, the movie follows her as she rebuilds the farmhouse — and her life. Whenever I feel down, this film lifts my spirits again and again.
6. Eat, Pray, Love
Continuing with the theme of traveling post-divorce, this film is based on the memoir by Liz Gilbert and follows her post-divorce journey around the world. Played by Julia Roberts, she eats in Italy, prays in India, and finds love in Bali. A feel-good romantic comedy, this film is essential for those who have just gone through a divorce and find themselves at a crossroads similar to Gilbert’s.
7. Mrs. Doubtfire
This film follows Daniel Hilliar (Robin Williams), an irresponsible dad with a heart of gold only allowed to see his kids for a short time each week. He soon finds out his ex needs a housekeeper, so he disguises himself as an English nanny named Mrs. Doubtfire and becomes the parent he should have been all along. The movie seems like an absurd comedy at face value but has a lot of hidden gems. A family favorite.
8. It’s Complicated
Marriage, divorce, then what? Jane Adler (Meryl Streep) and Jake Adler (Alec Baldwin) reunite 10 years after their divorce for their son’s college graduation, but a few drinks and a walk down memory lane puts them in, let’s say, a few compromising positions. The problem is that he’s married and she’s also starting a relationship. The result? Things get complicated. An exploration of the “what ifs” that come after divorce and how older children still reflect on their parents’ breakup, this film is both beautiful and brilliant. Not to mention hilarious in parts.
9. Gloria Bell
This movie is a drama about a divorced woman, played by Julianne Moore, who works an office job during the day and dances at clubs in Los Angeles at night, which results in her engaging in a new relationship. The film explores family, romance, and identity while offering stunning cinematography and a strong lead performance from Moore. A remake of a 2013 Spanish-language film, both are worth the watch because of the strong acting and even stronger message that your dance card has room on it for new partners after your divorce.
10. The Parent Trap
Starring Lindsay Lohan and, well, Lindsay Lohan, the film (also a remake) follows identical twins Hallie Parker and Annie James, who were separated very young as a result of their parents’ divorce. The sisters reunite at summer camp, realize that they are indeed twins, and plot to rekindle their parents’ relationship by switching places. It essentially plays out as every child of divorce’s fantasy, which is what makes it such a feel-good classic.
11. Crazy, Stupid, Love.
Comedy, romance, and drama are all wrapped into this one film. Here, Cal Weaver (Steve Carell), who seemingly lives an idyllic existence, is thrust into single life when his wife Emily (Julianne Moore) reveals she has been unfaithful and asks for a divorce. Over 40 and forced to re-enter the dating world, Cal encounters Jacob Palmer (Ryan Gosling), who teaches him how to navigate hookup culture and repair his lost confidence.
12. Enough Said
This film follows Eve (Julia Louis-Dreyfus), a divorcée on the verge of an empty nest, who wonders what is in store for her. She meets Marianne (Catherine Keener), a woman she interprets as the idealized version of herself, and is inspired to give her new romantic interest, Albert (James Gandolfini), a chance. The problem? Eve’s newfound friendships are a little too close for comfort.
13. Something’s Gotta Give
Harry Sanborn (Jack Nicholson) is an aging playboy who exclusively dates younger women, including his latest, Marin (Amanda Peet). However, while visiting her mother Erica’s (Diane Keaton) beach house, he suffers a heart attack, and it is up to Erica and his doctor (Keanu Reeves) to nurse him back to health. A love triangle forms, with its accompanying drama. An exploration of gender stereotypes in the divorce and dating worlds, as well as emotional unavailability, this movie will ring true for anyone who’s dipped their toe or jumped into the modern-day dating pool post-divorce.
14. When Harry Met Sally
Can men and women be just friends, or does the possibility of sex always get in the way? One of my all-time favorites, this film follows Harry (Billy Crystal), a skeptic on love since his divorce, and Sally (Meg Ryan) over 11 years as they struggle to determine the answer to this most highly-debatable question.
15. Marriage Story
What I would call an instant divorce classic, this film follows a stage director, Charlie (Adam Driver), and his actress-wife, Nicole (Scarlett Johansson), as they navigate a grueling divorce, all the while being on opposite sides of the country. Raw and emotional, the movie will have you crying and contemplating every relationship you’ve been in for hours afterward. More importantly, you will walk away with the realization of how every action you take during separation affects not only your soon-to-be-ex but also your kids.
16. The First Wives Club
“Don’t get mad. Get everything.” This comedy follows three middle-aged women (Goldie Hawn, Bette Midler, and Diane Keaton) from Manhattan who had helped their husbands achieve success in their work and social lives, only to get dumped for younger versions of themselves. They join forces and mastermind a ridiculous and insane but entertaining plan to get back at their exes. If you love empowering revenge films, this one’s for you.
17. Blue Valentine
This romantic drama explores a marriage that has reached its breaking point. Cindy’s (Michelle Williams) marriage to Dean (Ryan Gosling) seems like a match made in heaven from the outset. But, as the film explores the flaws of these characters and their marriage’s dynamic, suffice it to say you will need a box of tissues on hand.
“Her” is a concept film that explores a near future in which a lonely writer (Joaquin Phoenix) struggles to recover from heartbreak resulting from the end of his marriage. He buys an artificially intelligent operating system, “Samantha” (Scarlett Johannson), and an affair between them begins. The movie combines science fiction and romance and offers commentary on the state of technology in our world today, most poignantly how it brings us together while keeping us apart.
19. A Separation
This Iranian drama follows a married couple as they decide whether to improve their child’s life by moving to a foreign country or stay in their home country of Iran to care for a parent with Alzheimer’s. The story is complex and features morally ambiguous characters while exploring marriage, class, religion, gender, and Iranian society.
“Stepmom” is the ideal film for women who loathe their ex-husband’s new love interest. At the start of the movie, divorced mother-of-two Jackie (Susan Sarandon) is competitive with her ex-husband’s career-focused girlfriend, Isabel (Julia Roberts). But when Jackie is diagnosed with cancer, the two women must set aside their rivalry and put the children first, sparking an unlikely friendship.
21. Mr. Wonderful
An electrician, Gus (Matt Dillon), wants to achieve his childhood dream of buying an old bowling alley with some friends. However, he can’t afford to because of alimony payments to Leonora (Annabella Sciorra). To improve his financial picture, he comes up with a plan to find her a new husband so that he doesn’t have to pay alimony payments anymore, only to find out that he perhaps wanted a different outcome all along.
22. Hope Floats
In this rom-com, Birdee Pruitt (Sandra Bullock) is humiliated by her best friend on television, who she finds out is also sleeping with her husband. Birdee starts over by moving with her daughter to her small Texas hometown, only to face adversarial acquaintances. Lucky for her, she meets Justin Matisse (Harry Connick Jr.), with whom a romance blossoms.
23. Bye Bye Love
To finish off this list is the rom-com, “Bye Bye Love,” which follows recently divorced friends Dave (Matthew Modine), Vic (Randy Quaid), and Donny (Paul Reiser), who are trying to begin the next chapter of their lives. Each man has his specific problems, and the film follows their relationships as they take on those issues. Most divorce rom-coms typically portray women after divorce, so this film feels refreshing in that we see the male group perspective, an underrepresented group in the subgenre. It also serves as a gentle reminder of how divorce affects everyone going through one.