FILMS THAT HURT SO GOOD

I was the tender age of nine when I got my first taste of a broken heart. Surprisingly, the end of a week-long relationship with my fifth-grade boyfriend that same year wasn’t the cause. My parents took my me and my brother to Magnolia Theater to see the PG-13 film everybody was buzzing about. Miraculously, the Titanic kept my attention for the entire runtime of three hours and 14 minutes. I fell head over heels for Leonardo DiCaprio with the rest of the world while simultaneously being weighed down by the crushing historical tragedy. As a highly sensitive child, I held out hope for a redeeming Hollywood ending that never came. In Jack and Rose’s final moments, my young mind couldn’t fathom a world where they didn’t safely end up together. Lead characters weren’t supposed to die. How could I possibly untether the fictional characters from fact? (Mind you, Google wasn’t able to provide quick fact-checking back then). Their love story was as real to me as the wreckage found on the depths of the ocean floor. My world was rocked.

By the time the credits rolled, I was living in between two worlds- one foot was suspended in childhood and the other was stretching into adult territory. From my heartache, grew a penchant for more serious films about love and loss. I was tired of predictable happy endings. Any protective cushion in kid’s programming seemed like a sham. The raw and tender variety were a more honest depiction of real life, not to mention a hell of a lot more interesting.

Call it a coping mechanism, but sometimes observing someone else’s crappy scenario makes our own seem less crappy in comparison. During puberty I was under the impression that if I studied these teen and R-rated dramas hard enough, I could navigate through life easier. Witnessing the anguish and longing firsthand prepared me for when real heartache eventually met me at my doorstep. Like many other children of the nineties, television and movie screens were a babysitter. A teacher.

If you’re anything like me, you’ll find the emotional hangover strangely satisfying. Like returning to an ex you know is bad news, I regularly revisit my broken hearts through my film rotation. Please enjoy my go-to recommendations that hurt so good.

Eternal Sunshine of the Spotless Mind

After a painful breakup, shy and risk-averse Joel and impulsive, quirky Clementine undergo an elective procedure to erase their memory of each other. Desperate to call the whole thing off mid-way through, Joel realizes happiness is worth remembering even if it’s temporary. 

At first glance, Jim Carey and Kate Winslet may appear like an odd pairing (the same can be said of her and Jack Black in The Holiday) but if you’ve seen either you realize that something about them together makes perfect sense. I stand by my claim that both actors give the best performance of their prolific careers.

The non-linear storytelling is told from the inside of Joel’s mind — a jumbled up knot of overthinking, past arguments, tender moments and the regret of walking away. The watching experience feels like a fever dream and for me, a hit of nostalgia since I’ve revisited it every year since high school. It’s weird and trippy and emotionally exhausting at times but, I do consider it a deeply thought-provoking romance at its core. When it’s over, it just might give you a strange urge to visit Montauk.

Like Crazy

At the height of their whirlwind romance, an expired student visa wedges thousands of miles between Anna and Jacob. Their once young care-free relationship spent intertwined with each other all summer is put to the test as they navigate the uncertainty of long distance. Budding careers and the flourishing social life of twenty-somethings adds a complexity to the plot that deeply resonated with me.

It was comforting to come across this film while in the throes of my own long distance relationship. No one in my friend circle was experiencing one at the time. In a way it was like having something to compare notes with. I was less alone.

This is a classic example of a movie that makes you forget you’re watching one. You feel like a fly on the wall in their relationship with the naturalistic script and improv giving it a veil of sincerity. I gather they were each other’s first serious relationship. Their inexperience came off in in a very believable way. Moments of tension grow slowly from scene to scene. So much is revealed by their body language and the stretches of silence. The patient pacing of the film feels like watching their love unfold and fall apart in real-time.

Blue Valentine

An examination of the crumbling marriage between working-class parents Cindy and Dean. The ghost of their budding relationship follows them around as it weaves in and out of their hopeful past.

Ryan Gosling as Dean, and Michelle Williams as Cindy have an undeniable chemistry delivering raw and moving performances. Neither play a villain or a hero – just deeply complex and flawed individuals. One being already halfway out the door while the other begs them to stay.

The genuine performances of the small supporting cast felt as though they pulled real-people off the streets of New York, in the best way. Despite the A-list leads, the independent drama pulls back the curtain on Hollywood. It makes the whole experience feel so real, you can touch it. 

The stark contrast between their madly in love beginnings and their strained and distant current circumstances represent the way many people reflect on relationships nearing the end – in extremes. If you have a pulse at all, this film is guaranteed to put you in a funk. But I promise it’s not all depressing. A delightful ukulele and tap dancing scene will offer reprieve from the heaviness.