I watched Good Will Hunting for the first time last week and it's one of the best ways I’ve ever seen the experience of being a guy in your early 20s captured. Everything from how we deal with our emotions and talk about mental health, to how we act in relationships and avoid vulnerability in fear of how people will think of us differently was like looking in a mirror. I could understand exactly how the characters were thinking and feeling because I've been there many different times these past few years. Here are all of my thoughts on the movie and why I think every guy in their early 20s needs to watch it!

Why Every Guy in His 20s Needs to Watch "Good Will Hunting"

Some movies entertain you for a couple of hours, and some movies change the way you see yourself. It's rare to find a film that feels like it's looking directly into your soul, speaking to experiences you thought were uniquely yours.

That's exactly what happened when I finally watched "Good Will Hunting" for the first time, at 24 years old – nearly 27 years after its release. The experience was so profound that I had to dedicate an entire episode to dissecting why this 1997 film resonates so deeply with young men today.

Finding a Movie When You Need It Most

I'll admit it – I avoided watching "Good Will Hunting" for years. I'd always chalked it up as one of those universally beloved classics like "The Shawshank Redemption" that everyone praises, but I never felt compelled to see for myself.

That was a mistake.

What I discovered was a film that captured the experience of being a young man in your twenties with such precision that it felt like looking in a mirror. The characters, their struggles, and their behaviors reflected my own life with startling accuracy.

But here's what makes the movie's impact even more interesting: I'm convinced I watched it at exactly the right moment in my life. Had I seen it in high school or even college, I doubt it would have hit me with the same force. The post-college years of your twenties create a unique perspective that allows the film's themes to truly resonate.

Written By Guys Who Get It

Part of what makes "Good Will Hunting" so authentic is its origin story. Matt Damon and Ben Affleck were just 22 and 20 when they started writing the screenplay. When they won the Oscar for Best Original Screenplay, they were 27 and 25.

This wasn't a film about young men written by middle-aged Hollywood executives trying to remember what it felt like to be young. This was created by guys living through those exact experiences in real time.

The result is a movie that captures the essence of masculine identity in ways that feel almost uncomfortably familiar:

• The emotional unavailability we all struggle with

• The fear of vulnerability that keeps us isolated

• The tendency to avoid therapy and mental health support

• Our complicated approach to romantic relationships

• The way we use humor to deflect serious conversations

• The confusion about our future and purpose

The Fear Behind Our Toughest Challenges

At its core, "Good Will Hunting" explores something most guys in their twenties are dealing with, whether they admit it or not: the fear of being vulnerable.

Throughout the film, we see Will (Matt Damon's character) employ countless defense mechanisms to avoid emotional intimacy. He laughs at the suggestion of therapy. He sabotages relationships. He uses his intelligence as a shield.

Why? Because being vulnerable means risking rejection. It means letting someone see the real you – not the facade you present to the world, but your authentic self with all your flaws and quirks – and accepting that they might not like what they see.

This fear manifests in several key areas that resonated with me:

Relationships and Intimacy

The fear of falling in love and not having that love returned is something many of us struggle with. Dating in your twenties means putting yourself out there repeatedly, risking rejection, and confronting the possibility that someone might get to know the real you and decide they're not interested.

As Will's character shows us, it's often easier to avoid deep connection altogether than to risk being hurt. But the film also beautifully illustrates why that approach ultimately leaves us unfulfilled.

Mental Health and Therapy

When Will first hears about therapy, he laughs it off – a reaction that feels painfully familiar to many young men. Our generation has made strides in destigmatizing mental health support, but we're still fighting against deeply ingrained cultural messaging that seeking help is somehow a sign of weakness.

The film's portrayal of therapy as a path to healing rather than a mark of failure was revolutionary for its time and remains powerful today. Robin Williams' character shows that working through your issues takes more courage than burying them.

Finding Direction and Purpose

One of the most relatable moments in the film comes when Will is asked what he wants to do with his life. Rather than giving an honest answer, he deflects with sarcasm – masking his genuine uncertainty with humor.

This reflects the existential anxiety many of us feel in our twenties. We're supposed to have it all figured out, but many of us are still searching for purpose and direction. The pressure to know your path creates a fear of admitting you're still figuring things out.

Why This Film Matters Now More Than Ever

Despite being released nearly three decades ago, "Good Will Hunting" feels remarkably relevant to the challenges young men face today.

In some ways, our generation has made progress. Conversations about mental health are more common. The stigma around therapy has diminished somewhat. But in many fundamental ways, the core experiences of navigating early adulthood as a man remain unchanged.

We still struggle to process our emotions in healthy ways. We still fear vulnerability. We still use humor and avoidance to skirt around difficult conversations. And we still compare ourselves relentlessly to others, wondering if we're falling behind.

What makes "Good Will Hunting" so valuable is that it doesn't just reflect these struggles – it offers hope. It shows that growth is possible, that confronting your fears can lead to healing, and that vulnerability, while terrifying, is the path to genuine connection.

Required Watching for All Guys

If you're in your twenties and haven't seen this film, consider this your assignment. This isn't just entertainment – it's a mirror that will help you understand yourself better.

You'll recognize yourself in these characters. You'll see your own defense mechanisms laid bare. You might even find yourself emotional at moments that hit unexpectedly close to home.

More importantly, you'll be reminded that you're not alone in these struggles. The experiences that feel most isolating – the fears, the uncertainties, the reluctance to open up – are universal parts of becoming a man.

And perhaps most valuably, you'll see that there's a way forward. That working through your "shit" (as Robin Williams' character would say) isn't just possible – it's necessary for becoming the person you want to be.

Final Thoughts

Movies find us when we need them. For me, watching "Good Will Hunting" in my mid-twenties provided clarity about experiences I was actively navigating.

The film reminded me that getting to choose who you let into your "weird little world" is what life's about. That facing your fears – whether in relationships, therapy, or career choices – is where growth happens. And that vulnerability, while terrifying, is the path to the connections we all desperately need.

So if you haven't seen it yet, make it a priority. And if you have, maybe it's time for a rewatch with this new perspective in mind. Either way, I'd love to hear how it resonates with you.

What movies have profoundly impacted your understanding of yourself? I'd love to hear your recommendations for films that capture the experience of being a young man today. Email me at josh@guyset.com or DM me on Instagram @theguyset.

Want to hear the full episode? Listen to my "Good Will Hunting" breakdown on Apple Podcasts, Spotify, or wherever you get your podcasts. You can also follow along on Instagram and TikTok @theguyset for more content.

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See you guys next Tuesday.