"As a woman who’s currently in her 20s, nothing about this time in my life has gone the way I thought it would. That’s not necessarily a bad thing. Taylor Swift said it best: “We’re happy, free, confused, and lonely at the same time.” But one thing that has always brought me comfort in a tough situation is seeing myself reflected in a piece of media—especially on my TV screen. Knowing what movies to watch in your 20s is a key way to feel seen in one of the most confusing times of life.
Breakups, career trouble, or trying to figure out what you want to do with your life: You name the 20s struggle, and there’s probably a movie about it. Seeing characters go through a similar experience helps me realize that I’m not the only one who feels like I don’t have it together. Whether it’s a popular rom-com or something more artsy, these are the movies to watch in your 20s featuring main characters who are just like us.
1. Legally Blonde
Of course, I had to start this list off with the ultimate “girl power” movie. After a devastating breakup, sorority girl Elle Woods (Reese Witherspoon) follows her ex to law school. But in her attempts to win him back, she finds a new passion in the courtroom instead. Not only is ‘Legally Blonde’ arguably one of the most iconic romcoms, it’s also a great example of how your 20s are the perfect time for self-discovery. Sure, you probably (definitely) shouldn’t change your entire career path over one person, but in Elle’s case, she learned that she could do anything she set her mind to and was unapologetically herself while doing it—hot pink jumpsuits and all.
2. Before Sunrise
Your 20s are such an easy time to romanticize, and movies like ‘Before Sunrise’ only make it easier. When Jesse (Ethan Hawke) meets Celine (Julie Delpy) on a train to Vienna, the two instantly click and decide to explore the city together for one magical night. How many of us have seen someone cute at an airport and imagined an entire scenario where they end up in the seat next to you on your flight? This movie takes that storyline and puts it on the screen, showing us that while not every person will be in your life forever, someone can still have a big impact on your life despite only knowing each other for a short time.
3. Booksmart
On the day before their high school graduation, best friends Molly (Beanie Feldstein) and Amy (Kaitlyn Dever) realize they spent too much time studying. To get the true teenage experience before graduation, they decide to go to the biggest party of the year. While the characters in ‘Booksmart’ are a little younger, watching them scramble to straighten out their priorities is both hilarious and relatable for those of us twentysomethings who feel pressured to have all the answers. The ways that Molly and Amy are pushed out of their comfort zones also help viewers realize that trying new things isn’t always as scary as you’d think.
4. Lady Bird
Christine “Lady Bird” McPherson (Saoirse Ronan) wants nothing more than to get out of Sacramento. During her senior year of high school, she tries out for new clubs, meets new friends, and falls in love, all while imagining a life for herself on the other side of the country. As much as ‘Lady Bird’ is a story about mothers and daughters—another relevant topic for this list—it’s also about finding your home away from home. The first real step of adulthood is living on your own and learning to take care of yourself. Whether it happens while you’re in college or later, sometimes it takes leaving your hometown in order to gain a deeper appreciation for where you came from.
5. Tick, Tick… Boom!
Based on the musical of the same name (and the true story of the man who wrote it), ‘Tick, Tick… Boom!’ follows Jonathan Larson (Andrew Garfield) on his crusade to become the next big thing in musical theater. While it’s the only movie on this list with a male protagonist, Jonathan’s story deals with a struggle I think many twentysomethings can relate to: the pressure to get everything right. Jonathan’s first musical may not have been a hit, but he went on to write ‘Rent,’ which ran for over a decade on Broadway. ‘Tick, Tick… Boom!’ teaches us that even if we don’t nail it on our very first try, we’re all capable of great things.
6. 13 Going On 30
When teenage Jenna Rink (Jennifer Garner) makes a wish to be older, she’s surprised to wake up the next morning in a completely different body and with a completely different life. It’s a dream come true at first, but as she gets to know who she’ll become in the future, it makes her reevaluate whether growing up is all it’s cracked up to be. ‘13 Going On 30’ is a perfect movie for women in their 20s not just because it shows us how to reconnect with our inner child, but it also serves as a reminder that you can’t rush through certain parts of your life because you think the future will be better.
7. The Devil Wears Prada
With its iconic outfits and so many quotable moments, ‘The Devil Wears Prada’ is both a classic dramedy and a warning for women just entering the workplace. Journalist Andy Sachs (Anne Hathaway) lands a coveted job as the personal assistant to Miranda Priestly (Meryl Streep), editor-in-chief of Runway magazine. It’s not what Andy wants long-term, and her boss is horrible, but what’s worse is the way she loses herself in the never-ending fight to please Miranda. This movie’s message is especially relevant to twentysomethings early in their career. It’s OK if your first job isn’t your forever job, but you are so much more than your work.
8. Little Women (2019)
Another movie that simply had to be included. ‘Little Women’ follows the March sisters—Meg (Emma Watson), Jo (Saoirse Ronan), Beth (Eliza Scanlen), and Amy (Florence Pugh)—growing up in Civil War-era New England. Even from a young age, the four girls each know what they want out of life, and watching them achieve their dreams shows us just how many possibilities are at our fingertips. Whether you strive to be remembered like Jo or just want to settle down like Meg, the choice is yours to make. A story that’s so rooted in sisterhood obviously has a lot to say about family, too. As the girls grow up, their relationship may look different, but their bond never wavers.
9. Romy & Michelle’s High School Reunion
There’s a good chance that the way you imagined your adult life as a high schooler is wildly different from your current reality. Such is the case for best friends Romy (Mira Sorvino) and Michelle (Lisa Kudrow), who realize they haven’t done much since graduating high school and pretend to be successful businesswomen at their 10-year reunion. As hilarious as this movie might be, its message hits home for those of us still trying to figure out who we want to be. There’s no point in pretending to be someone you’re not, especially if you’re doing it to win other people’s favor. It doesn’t matter what anyone else thinks of you—only what you think of yourself.
10. Past Lives
Over their decades-long friendship, Nora Moon (Greta Lee) and Hae Sung (Teo Yoo) are repeatedly drawn together and pulled apart, always on the brink of something more. When they reconnect in person for the first time since Nora left Korea when she was younger, she’s forced to come to terms with the many different ways her life could have played out. ‘Past Lives’ is as much about sacrifice as it is a love story. As an immigrant, Nora’s decisions are shaped by the different versions of herself she had to leave behind—both who she was and who she could have been. That “what if” is what makes ‘Past Lives’ so devastatingly beautiful and relatable to women in their 20s watching.
11. Sisterhood of the Traveling Pants
Right before their first summer apart, Carmen (America Ferrera), Bridget (Blake Lively), Lena (Alexis Bledel), and Tibby (Amber Tamblyn) find a pair of jeans that fit them all perfectly. They decide to share the pants, documenting the adventures they each have while wearing them. Even though they’re rarely in the same room, the girls’ friendship is still so strong and intentional. Their individual stories are just as compelling, from Lena’s forbidden romance to Carmen’s complicated relationship with her father to Tibby’s and Bridget’s experiences with grief. ‘The Sisterhood of the Traveling Pants’ celebrates female friendships and the idea that sometimes family is what you make it, rather than what you’re born into.
12. Someone Great
Rom-coms about breakups always hit harder than regular romances, and ‘Someone Great’ is one of the most underrated movies in this category. Jenny (Gina Rodriguez) is fresh out of a decade-long relationship and on the brink of moving across the country to start a new job. As one last night out, she and her friends Erin (DeWanda Wise) and Blair (Brittany Snow) run around town hoping to score tickets to a big musical festival. Saying goodbye to the people and places we love is never easy, but this movie portrays the “transition stages” of adulthood so well that you’ll laugh as much as you cry while watching.
13. How To Have Sex
Best friends Tara (Mia McKenna-Bruce), Em (Daisy Jelley), and Skye (Lara Peake) go on vacation for a week in Greece with plans to party every night. But what starts out as the best summer ever becomes something darker when Tara disappears for a night. This movie deals with societal pressure surrounding sex, since Tara is the only virgin in her friend group, and its discussion of consent might be triggering to some. Navigating sex and relationships in your 20s is about having fun, but more importantly about learning what you are and aren’t comfortable with, especially when it comes to a partner. Even though ‘How to Have Sex’ is a hard watch, it’s also a worthwhile one.
14. Rye Lane
I know we single girls are tired of hearing that love will find us when we least expect it, but that’s exactly what ‘Rye Lane’ tells you–and honestly, I’m not mad about it. Twentysomethings Dom (David Jonsson) and Yas (Vivian Oparah) meet soon after being brutally dumped by their respective exes and help each other through the heartbreak. Despite how unconventional it would be in real life to fall for the person who caught you crying over your ex in the bathroom, this British rom-com portrays it in a way that feels realistic alongside the awkwardness of moving on.
15. Frances Ha
Frances (Greta Gerwig) is a would-be dancer in her late twenties living in New York with her best friend Sophie (Mickey Sumner). When Sophie announces she’s moving out, Frances is left scrambling to find a place she can afford on an apprentice’s salary. She may not have a lot of money or a steady job, but she’s doing what she loves and has her friends in her corner, and that’s what matters. This time of your life is unpredictable and messy, and it’s supposed to be—that’s what makes it so much fun. Someday the struggles will make more sense, and then everything will have been worth it.
ABOUT THE AUTHOR
Hannah Carapellotti, Contributing Writer
Hannah is an Ann Arbor-based writer with a bachelor’s in English and writing from the University of Michigan. Outside of The Everygirl, Hannah has written for The Michigan Daily, where she also served as an editor. She currently works at an independent bookstore and is interning for a literary agency.