20 films you need to watch in your 20s

Ah, to be a twenty-something! Our twenties are such formative years: the decade of life where we still make some version of high school mistakes, but have the bank account and appropriate age credentials to go have a drink afterwards and commiserate about it. There are so many movies that realistically and/or entertainingly convey the emotions and experiences that happen at this time in our lives, but here are twenty of them that I think every twenty-something needs to watch.

Eternal Sunshine of the Spotless Mind

This movie highlights how imperfect we all are when it comes to relationships. We’re human. We make mistakes. And even if we sometimes think it would be easier to just erase something from our minds, it’s important to remember that whether it’s joyous or painful, every experience shapes us. Our suffering and our ecstasy help us to know what we need to move forward. This movie is the ultimate reminder that we have to take the good with the bad in order to grow and experience true love.

Frances Ha

Sometimes it takes an unexpected kick from a friend to force us into discovering ourselves and what we should be doing with our lives. Greta Gerwig as 27-year-old dancer Frances ends up forced to do so when her best friend moves out of their apartment to live with her boyfriend. She travels all over (NYC and the world!) and works odd jobs, just to realize she had everything she needed for a satisfying existence right where she started. Sometimes you need to escape—whether geographically or emotionally—before you can appreciate what’s available to you at home.

Working Girl

Every one will, at some point in their professional life, feel unfairly minimized. Regardless of the fact that it’s 2015 and the 80s hairstyles and clothes of this movie are mostly a thing of the past, the actual message behind it is forever relevant: you have to fight for your chance to be heard. It’s all about working incredibly hard and using your creativity to get ahead in life! (Bonus: it will make you really really want to ride the Staten Island Ferry while blasting the film’s title song by Carly Simon.)


It’s so easy to mistake infatuation for love in our twenties (or, you know, at any age), but love isn’t about being readily available in case the object of your affection happens to throw a glance your way. In this film, Sabrina allows an infatuation to consume her so much that she’s not even living her own life. But she eventually realizes she has her own talents to nurture, and creates a life for herself outside of swooning over a man who barely notices her. It’s only when she focuses on herself that she can see what it’s like to love someone who deserves her attention and have her feelings wholeheartedly reciprocated.

Someone Like You

A movie about the three B’s: boyfriends, besties, and breakups! Ashley Judd plays a character so despondent over the end of her relationship that she seeks out a scientific theory just to explain why it happened. The dashing Hugh Jackman swoops in to help force her to accept the breakup, and that she’s in no way lacking or less than whole because of it (which we’ve all felt when our ex has moved on to someone new). Plus, Marisa Tomei plays her BFF, and they have the most relatable relationship post-mortem conversations ever.

Reality Bites

This movie is the quintessential summarization of life post-college. It’s the time when we are all figuring out how to pay rent and, more importantly, how to find a fulfilling job to pay that rent. It has some very real depictions of friendship, heartbreak, and discovering one’s sexuality and sexual responsibility (plus entertaining calls to a psychic hotline). It also reminds us that the only thing we will always remember after college graduation is our social security number.

(500) Days of Summer

Sometimes the truth becomes a lie: that’s the best way to explain the phenomenon of a person saying they don’t want a relationship, and then seeing them a short time later happily in one with a person who is not you. It’s a scenario that will happen to everyone in their twenties and beyond, and this movie nails every emotion that goes along with it.

Blue Valentine

This film is in some ways similar to (500) Days, but takes it to the next level: marriage. Most people are constantly evolving throughout their lives, but so much of that change happens in our twenties and it can make sustaining a relationship difficult. Adjusting to each other’s growth in terms of wants and needs takes work. If one person has new dreams and the other is content with everything staying the same, whose fault is it if it doesn’t work out? That’s the all-too-real issue this movie delves into with incredible performances by (swoon) Ryan Gosling and Michelle Williams.

Something Borrowed

Based on the book of the same name by Emily Giffin, this movie encapsulates what happens in the lifelong friendship of Rachel and Darcy, when one person always compromises on what she really wants and needs. It’s a pattern that can easily be settled into during childhood, but true friendship adapts with age, and Rachel finally learns to speak up for what she wants instead of accepting the role of standing in Darcy’s shadow. (The sequel, Something Blue, which isn’t a film yet, tells Darcy’s side of the story.)

In Her Shoes

As a kid, your sibling is someone to play with, fight with, and band together with against your parents. In your twenties, you look out for each other, and even if you fight, you’re one another’s strongest connection to your past. This adaptation of Jennifer Weiner’s book shows the highs and lows of a tumultuous but strong relationship between two sisters through breakups, unemployment, family drama, and broken designer shoes.

When Harry Met Sally

An iconic movie to watch at any time and at any age, it truly did resonate in my twenties because the majority of the film takes place during that age span for the title characters. They ponder whether men and women can truly be “just friends” and they prove that the strongest romantic relationships can spring from a platonic foundation.

Up in the Air

This film pits Anna Kendrick against George Clooney in a way that is all too familiar in the workforce: a twenty-something with fresh ideas wants to streamline age-old business practices and update a company to the 21st century. Anna’s character is bright and talented, as is George’s, but they butt heads on some fundamental issues on how to best do their jobs. Finding ways to improve is always a plus in any business, but so is learning from someone with years of experience—and this film is chock full of job lessons for the recent college grad. The movie also promotes the idea that taking risks in love and life may not always turn out as you hope, but they’re usually worth taking, anyway.

Crazy, Stupid, Love

You didn’t think I was only going to mention Ryan Gosling once, did you?! Even though the RyGos–Emma Stone relationship is the most relatable to a twenty-something, this movie is a really fun, funny, and sweet ensemble romantic dramedy overall. As varied as all the characters are, it simply drives home the universal truth that no matter what, everyone is always just searching for love and a real human connection, no matter your age.

The Devil Wears Prada

Darlings Anne Hathaway and Emily Blunt do battle against the wicked Meryl-Streep-as-Miranda-Priestly! That first job out of college can be tough. And many times it’s not what you really want for your career. But sometimes rent has to be paid, or you need to make connections so you can get closer to your dream job, and you end up with a horrible boss whom you have to tolerate for what seems like an interminable amount of time. It’s all a very real part of being an adult, and this movie helps us laugh at it.


This movie featured incredible performances by Gabourey Sidibe, Mo’Nique, Paula Patton, and Mariah Carey. It’s a very realistic look at sexual, physical, and emotional abuse, and full of inspiring moments that make you feel like you can fight to overcome any terrible obstacle thrown your way. My heart broke for Gabourey’s character as she tried to prevail against abuse from the people who were supposed to protect her. But sometimes, when you can’t turn to your own family, it’s still possible to build a makeshift one through friends and members of your community.

Obvious Child

The brilliant and funny Jenny Slate stars in this film broaching subjects that typically aren’t explored with nuanced honesty and humor. There’s no other movie in existence that tells you it’s okay to not be ashamed for choosing to have an abortion; but more importantly, it brings up the fact that women should always have a choice for what happens to their own bodies.

The Way Way Back

Sam Rockwell makes me swoon Ryan Gosling-style in this movie. Like Crazy, Stupid, Love, it’s another stellar ensemble cast in a dramedy that follows all different kinds of relationships—including familial, romantic, and, most importantly, a type of mentorship. Liam James plays Duncan, an unhappy teenager who has no confidence or friends, and Sam Rockwell takes him under his wing and gives him a summer job so he can really come out of his shell. The confidence Duncan builds at this job leads him to form a better relationship with his mother and a friendship with his summer crush. The film reminds us that, even if you’re a confused twenty-something, if you can reach out to someone younger who is struggling, it can make a world of difference.


Real life friends Maya Rudolph and Kristen Wiig play besties Lillian and Annie as they prepare for Lillian’s upcoming wedding and disaster ensues. Your twenties will be full of dating jerks (probably none that look like Jon Hamm, though), watching friends get married before you, and self-sabotaging relationships with nice people. This movie is funny, poignant, and makes you want to call your best friend immediately. (And possibly adopt seven puppies.)

Steel Magnolias

I read once that the title was meant to evoke the incredible strength a woman possesses while still outwardly seeming as delicate as a magnolia flower, and that’s essentially the heart of this movie for all the female characters. They power through situations as devastating as death or as silly as a bad hair day with consistent grace, humor, and dignity. Friends become a secondary kind of family in your twenties. The friendship bond in this film will consistently make you cry every single time you watch it, and that’s totally a great thing. It will also make you wish Dolly Parton ran your hair salon.

The Princess Bride

It’s important to watch this movie in your twenties (and as you get older) because it’s always good to keep your heart open to fairytales. The optimism and fantasy of a fairytale is something that we can always use no matter our age. We will never be too old to say, “My name is Inigo Montoya, you killed my father, prepare to die,” and about a thousand other quotes that we all could recite in our sleep. And as the story goes, there was no purer love than Westley and Buttercup, which means that watching this movie with our significant other might give them some help in the romantic gesture territory. (Aside from the whole having to die and come back to life with a magic chocolate pill thing).

So what did I forget? Tell me what you would add to the list!