Crazy Ex-Girlfriend and the Sisyphean Pursuit of Happiness

Rebecca Bunch, the protagonist of The CW’s musical romantic comedy Crazy Ex-Girlfriend, shows how pursuing happiness alone is as vain as grasping for vapor in the wind. As the award-winning show concludes its fourth and final season, it’s worth reflecting on Rebecca’s journey of emotional growth and the lessons it offers for our everyday lives. (Warning: this essay contains spoilers.)

Rebecca is an ambitious and successful lawyer at a big firm in New York, yet after a chance encounter with Josh, her ex-boyfriend from summer camp 10 years prior, she impulsively decides to quit her job and life in New York to move across the country to Josh’s hometown: West Covina, California. Thus begins her single-minded aim of winning him back.

The entire first season revolves around her hysterical and outlandish antics intended to make Josh fall back in love with her. “Chance” encounters, befriending Josh’s current girlfriend to get close to him, dating Josh’s best friend to convince people she isn’t romantically interested in Josh, renting a fully loaded RV for a trip to the beach to get Josh’s friend group to want to spend time with her, the list of her absurd lengths goes on. All the while she simultaneously denies to herself and others that these efforts — let alone her move to a relatively unheard-of town in California (West Covina: only two hours from the beach! Well, four in traffic…) — have anything to do with Josh at all.

It’s only at the end of season one that Josh finally decides that Rebecca is who he wants to be with, and it isn’t until the middle of season two that Josh finally proposes. (In a dramatic scene dripping with irony, Rebecca is in a session with her therapist, who was on the brink of helping Rebecca decide to focus on personal growth and not look for validation on men, when Josh bursts through the door and asks for her hand — ensuring that all the therapist’s work is stunted.)

Finally Rebecca has everything she’s ever dreamed of. She and Josh are engaged and preparing to spend their lives together forever. This dream that has possessed her since that fateful chance run-in with Josh — that dream that she’s lied, stalked, manipulated, skulked, and even moved to West Covina for — has finally materialized.

Yet, she is dissatisfied. Things aren’t right. Having won Josh, and planning their new life together, is not quite what she thought it would be — what she dreamed and hoped it would be. In fact, she finds herself desperately attracted to her boss. When they find themselves trapped in an elevator, she is overcome by temptation and kisses him passionately.

Filled with guilt at her unfaithfulness to Josh, and still convinced that her marriage to Josh will fill the gaping void in her soul, Rebecca bribes a bride at her and Josh’s dream wedding venue to give up her wedding — planned for next week. Of course, she tells Josh the date “just happened” to open up, but this rush to the altar precipitates an unfortunate series of events that [SPOILER] ends with Josh leaving Rebecca at the altar — and reveals that Rebecca suffers from a history of mental illness and has previously been institutionalized for stalking and burning down the home of a past lover when she was in college.

“Vanity, vanity,” claims the wise man of Ecclesiastes, “all is vanity… chasing after the sun.”

Crazy Ex-Girlfriend has been praised for its realistic depiction of mental illness. Viewers are saddened to learn of Rebecca’s deeply troubled mental state. Yet what makes Rebecca so endearing is the relatability of her madness, her obsession, her dedicated pursuit of what she wants — and more importantly, her disappointment when she realizes that attaining the object of her desire isn’t as satisfying as she’d originally hoped.

One doesn’t need a diagnosis to struggle with the misplaced loves and the inevitable disappointment that follows when they don’t live up to expectations. We can all relate to this. We all suffer from the same sickness of the soul — of allowing our desires to define us, and justifying outrageous, and even self-harmful, ends in order to achieve them.

Our entire culture is geared toward promising us that what will ultimately fulfill us is one purchase away. It promises the eternal in the temporal. This is inevitably a lie, yet we strive and grasp anyway in hopes that it isn’t.

“One must imagine Sisyphus happy,” declared existentialist philosopher Albert Camus after deciding the futility and frailty of life. In Greek mythology, King Sisyphus displeased Zeus — ruler of all gods on Mount Olympus — so greatly that Zeus condemned Sisyphus to a lifetime of rolling a boulder up a hill, only to have it roll down again and repeat the process when he reached the top. This is in many ways a fate worse than death: an existence of utter futility.

This, it often seems, is what we are condemned to, too: we have longings that are far deeper, richer, and more transcendent than can ever be met by the superficial offerings of this world. When we expect too much of this world — when we expect our eternal needs to be met temporally — we are both invariably disappointed and also ultimately crush the object of our desire with our expectation.

In Camus’ declaration, he meant that while life is utterly meaningless, we must create our own meaning and happiness despite its pointlessness.

Rebecca tried that, and it didn’t work. The trouble is that meaning and happiness is more elusive than we realize, and the costs of pursuing such a moving target may prove higher than it’s worth.

Dissatisfaction is baked into the human experience, keeping us all forever on the move, on the hunt, looking for the next thing. As tragic as this is, it is here we find the source of progress in the world, the unending search for a better life. And it is always a search, one that requires a social template of freedom and experimentation, not with the goal of nirvana but the goal of experiencing hope and opportunity.

I wish I could tell you that the show had a more satisfying conclusion.


At the end of season four, Rebecca has not just one, but three gentleman — including Josh — declaring their love for her. Rebecca, in a move that feigns evolved enlightenment, rejects them all, claiming that she realizes that a man isn’t going to fulfill her. This is true, and viewers begin to have hope that finally Rebecca might choose to focus on herself instead of looking to external circumstances and people for validation.

But instead, she decides to throw herself into a career in musical theater — her true dream, she finally realizes (the musical numbers throughout the seasons — they vary in quality, but most of them are light and witty and fun — are all vignettes that occur inside her head).

However, this is pernicious because, though it’s lovely she’s found a passion, the danger of placing careerism at the center of one’s identity and one’s affections is just as perilous as wantonly pursuing a man. It doesn’t matter what the substance is. An addictive personality will always be an addictive personality. In the end, it seems, sadly, Rebecca replaced one unhealthy affection with another.

Crazy Ex-Girlfriend has great dialogue, a consistently fast-paced plot (though thankfully not breakneck like the final season of Game of Thrones), and Rachel Bloom — who plays Rebecca Bunch — is hysterical. And, of course, it is encouraging to see such a raw depiction of the good, bad, and ugly of mental illness.

But I would be remiss to praise it without also highlighting the show as an important omen for our times: that the pursuit of our struggle for each day is, in fact, Sisyphean.