3 Movies That Are Perfect For Anyone Feeling Lost In Their 20s

Here’s the thing: You’re not supposed to have everything figured out about your life in your 20s. Your 20s are a decade meant for self-discovery, messing up, and adventure. However, that doesn’t mean your 20s are easy. Your 20s can actually be some of the most difficult and trying years of your adult life. I know my 20s were rough for me.

But no matter how unmoored you may feel, you’re not alone in your experience because I’d argue most of us feel lost in our 20s. Here are three movies that perfectly represent feeling lost in your 20s.

1. Good Will Hunting (1997)

Good Will Hunting is a classic for a reason. Starring Matt Damon, Ben Affleck, and Robin Williams, Good Will Hunting tells the story of Will Hunting (Damon), a janitor at MIT with a hidden mathematical genius. When Professor Gerald Lambeau (Stellan Skarsgård) writes a seemingly impossible math problem on a blackboard in MIT’s hallways, his students are stumped. However, when Will thought no one was around, he solved the formula, revealing his brilliance. When Professor Lambeau calls after him, Will sprints away.

Despite his vast intelligence, Will often finds himself in trouble. After getting into a street brawl that leads to yet another arrest, Will is almost sent to jail. However, Professor Lambeau hears about Will’s trial and shows up to bail him out. The condition? Will must work with Professor Lambeau on math every single week, as well as attend therapy. 

After several therapists give up on Will, his last shot is Sean (Williams), a friend of Professor Lambeau. It’s then that Will begins to face his demons, forgive himself, and ultimately find his purpose and himself in the process.

A real tear-jerker, Good Will Hunting is a movie about self-worth, redemption, and the power of someone else believing in you when you can’t seem to believe in yourself.

2. Garden State (2004)

Garden State is a coming-of-age indie film starring Zach Braff as Andrew Largeman, an aspiring actor who returns home to New Jersey from Los Angeles after the death of his mother. Andrew has not been home in many years, desperate to leave his past behind. Andrew’s mother had been a paraplegic due to a freak accident Andrew blames himself for. Because of the pain, Andrew’s father, a psychiatrist, put Andrew on a slew of antidepressant medications in an attempt to try to help his son recover from the trauma. However, the SSRI cocktail simply led Andrew to become completely numb to feeling anything at all.

However, when Andrew returns to New Jersey for his mom’s funeral, he goes off his medication cold turkey and begins to experience life again. With the help of old high school friends and free-spirited, quirky Sam (Natalie Portman), Andrew begins to open himself up to life once more. 

3. The Incredible Jessica James (2017)

Truly one of the most underrated movies on Netflix, The Incredible Jessica James stars Jessica Williams as Jessica James, an aspiring playwright with high walls around her heart after a devastating breakup. While she struggles to make sense of the heartbreak, Jessica continues to submit her plays to production companies, only to receive rejection after rejection (all of which she hangs up on her wall). 

Eventually, Jessica’s best friend sets her up on a date with Boone (Chris O’Dowd), a recent divorcee and app developer. Despite the incredible awkwardness of the evening, the two strike up an unlikely friendship and help each other move on from their exes. The Incredible Jessica James is hilarious, heartfelt, and relatable to anyone navigating their 20s with a broken heart.

About the author

Molly Burford

Writer. Editor. Hufflepuff. Dog person.