Love ‘The Parent Trap’? Here Are 14 Movies You Should Watch Next

When I was a kid, every time I went to summer camp, I searched the crowd for my identical twin. Unfortunately, I do not have an identical twin, but I secretly hoped that I did. Why? Because of The Parent Trap. I watched that iconic ’90s film (which was a remake of the 1961 original) over and over again. Not only did I love the premise of kids life-swapping and tricking their parents into falling back in love, but it also just made me so happy every time I watched it. The warm and fuzzy, yet funny and relatable themes of the movie were in many ways due to filmmaking genius Nancy Meyers.

Nancy knows how to tap into nostalgia and play our heartstrings. Her movies like The Parent Trap always leave the audience feeling like the kids-at-heart we’ll always be as adults. To be honest, I’m still holding out hope that one day I will discover I have a twin. And I have Nancy to thank for that, in the best way. If you love The Parent Trap too and want more movies that tap into the same nostalgia, unlikely scenarios, and ’90s meets early 2000s vibes, this list is for you. Here are some of the best movies that feel like The Parent Trap:

1. Freaky Friday

Lindsay Lohan was a key component to what made ‘The Parent Trap’ so great. Her breakout performance as both twins Hallie and Annie was iconic at the time (and still holds up). Lindsay went on to star in many hit movies, one of which was “Freaky Friday”. In the movie, Lindsay’s character Anna and her mom Tess, played by Jamie Lee Curtis, don’t understand each other at all. Some magic ensues, and suddenly the two have body swapped, having to literally live in the other’s shoes. While the premise of swapping lives is similar to ‘The Parent Trap’, it’s the relationships, comedy, and heartfelt moments that give this movie the same nostalgic vibe.

2. Now and Then

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‘Now and Then’ is at the top of my list for nostalgic movies. It follows four grown-up friends as they look back on a childhood summer in the 1970s. It’s a coming-of-age story that explores friendship, adventure, and facing change. It also has an incredible cast in both the younger and older versions of each of the characters, including Christina Ricci and Rosie O’Donnell. Best of all, the younger characters ride around everywhere on bikes, making mischief as they see fit. Much like the camp scenes in ‘The Parent Trap’, there’s a carefree vibe that will have you dreaming of childhood summers.

3. To All the Boys I’ve Loved Before

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With a classic “let’s pretend that we’re together” plot combined with love letters that weren’t meant to be sent out, this movie is for anyone who loves a YA rom-com. You can also read the original books that author Jenny Han wrote to get more of the story. The plot follows Lara Jean navigating high school as her crushes suddenly learn how she feels about them. If you loved rooting for Hallie and Annie’s parents getting together, you’ll be rooting for Lara Jean to be true to herself, regardless of whether she ends up with any of the boys she loved before.

4. Akeelah and the Bee

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If you love a spelling bee, or just can’t get enough inspirational stories, this movie is for you. ‘Akeelah and the Bee’ is set in the early 2000s, and follows an 11-year-old girl named Akeelah, played by the incredible Keke Palmer, who learns that she has a high aptitude for spelling. Laurence Fishburne plays a mentor that recognizes Akeelah’s talent and encourages her to keep entering contests, because he knows she has a chance at winning the National Spelling Bee. The story is nostalgic and inspiring as it conveys its overall message to let your light shine.

5. Prom Dates

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This movie just came out on Hulu, and stars Julia Lester, of ‘High School Musical: The Musical: The Series’, as Hannah and Antonia Gentry, of ‘Ginny & Georgia’, as Jess. While it takes place in our current time period, it gives off some real ’90s high school vibes. In the story, Hannah and Jess break up with their prom dates a mere 24 hours before the day, and start a quest to find new dates. Much like Hallie and Annie, the two always have some sort of plan to achieve their goals, but it doesn’t always go the way they thought it would. It’s funny, sweet, and ultimately makes the case that the most important relationships are our best friendships.

6. The Wedding Planner

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While not a Nancy Meyers movie, this movie has a lot of the same characteristics. It includes a lavish wedding, characters who are trying to find themselves, and a plot that puts the characters into impossible situations. It stars Jennifer Lopez (Mary) at the top of her rom-com game, and Matthew McConaughey (Steve), who was also on quite a run in the movie genre at the time. The movie follows Mary as she meets someone she has instant sparks with, only to realize that she’s about to plan his wedding. It’s one of my favorite J-Lo rom-coms, which really should be a genre on its own.

7. Father of the Bride

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‘Father of the Bride’ is yet another movie about a wedding, but was co-written by Nancy Meyers. The movie has an incredible cast with Steve Martin, Diane Keaton, Kimberly Williams-Paisley, Martin Short, and a very young Kieran Culkin. While the story takes place around a wedding, it’s really about the relationship of fathers and daughters, and moving on from childhood into adulthood. It will give you all the warm fuzzy vibes that Nancy Meyers movies like ‘The Parent Trap’ always promise, and will leave you wanting to be a wedding guest again ASAP.

8. The Lizzie McGuire Movie

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Like Lindsay Lohan, Hilary Duff was an icon of the early 2000s, thanks to the ‘Lizzie McGuire’ show. If you were a fan, you might also remember ‘The Lizzie McGuire Movie’ which takes Lizzie out of her hometown and into Rome, Italy. In Rome, Lizzie meets a famous singer named Paolo. She happens to look exactly like Paolo’s duet partner and in a very ‘Parent Trap’ plot twist, pretends to be the singer. While the movie is definitely targeted to a younger audience, it’s a fun, nostalgic rewatch as an adult in the same way ‘The Parent Trap’ is.

9. 13 Going on 30

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This movie takes its nostalgia all the way back to the late 1980s, where young Jenna makes a wish to be 30, flirty, and thriving like the women in the magazine she reads. In yet another magical body-swap moment, Jenna wakes up as the thirty-year-old version of herself, played by Jennifer Garner. She seeks out her childhood best friend Mattie, played by Mark Ruffalo, who doesn’t want anything to do with her after she became a mean girl in high school. The movie explores how getting what we wanted doesn’t always equal becoming the person we wanted to be. It has so many fun moments, a choreographed dance scene, and heartwarming twists as the younger version of Jenna influences the adult she becomes.

10. Life-Size 2

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Lindsay Lohan starred in the original ‘Life-Size’ with Tyra Banks back in 2000. In the movie (which has a Barbie twist, long before Barbie), a kid uses a magic spell that makes her favorite doll come to life. ‘Life-Size 2’ is a more recent sequel to the movie, starring Tyra Banks again as the doll named Eve and Francia Raisa of ‘How I Met Your Father’ and ‘Grown-ish’. Although it’s a more modernized take on the concept of a doll living in our reality (it came out in 2018), it also has the nostalgic vibes and heartwarming moments that are often so comforting when we watch movies from our childhood.

11. Turning Red

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This is an animated Pixar film, but watching it unfold is just as immersive as watching a live-action coming-of-age story. The movie follows 13-year-old Mei Lee growing up in the early 2000s as she balances adolescence with her changing relationship with her mother. On top of that, Mei turns into a giant red panda when she gets excited, leaving her to balance that, school, friends, and teenage angst. The nostalgia vibes are off the charts in this movie. If you had a friend group that was obsessed with a band, struggled with change growing-up, or sometimes felt like you didn’t fit in, this movie is for you.

12. The Holiday

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‘The Holiday’ is another Nancy Meyer’s classic that followed ‘The Parent Trap’ years later in 2006. While the movie takes place during the holidays, I stand by the fact that it’s a good movie to watch anytime of the year. In yet another life-swap premise (which I’ll honestly never get tired of) Cameron Diaz (Amanda) and Kate Winslet (Iris) play women who decide to switch houses for a holiday, to get away from their lives. While Iris goes to Los Angeles and discovers how to be the main character in her own life, Amanda goes to a tiny town in England and learns how to open her heart to new possibilities. It’s warm, it’s fuzzy, and it holds up today.

13. Mother of the Bride

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For a twist on unlikely parents falling in love, ‘Mother of the Bride’ follows Brook Shields (who has been having a moment with Netflix rom-coms since ‘A Castle for Christmas’) as she prepares for her daughter’s wedding. To her surprise, she realizes the father of the groom is the man who broke her heart in college. This movie just came out this year and also stars Miranda Cosgrove, Benjamin Bratt, and Chad Michael Murray who also, full circle, starred in ‘Freaky Friday’. It’s a fresh take on a wedding movie, has beautiful scenery, and of course, will have you rooting for your favorite couple to get together.

14. It Takes Two

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This list wouldn’t be complete without an Olsen twins movie. As actual twins, they made so many movies together it’s hard to pick just one, but ‘It Takes Two’ is probably one of the best. In a very similar plot to ‘The Parent Trap’, identical strangers Amanda and Alyssa meet in the woods. They form a plot to get their single (one about to be married) parents together, as they know they’ll be a perfect match. Kirstie Alley and Steve Guttenberg play the parents that have no idea their daughters are plotting together. If you loved ‘The Parent Trap’, you’ll love the mid-’90s twin caper vibes of this movie, too.

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