The Particular Pain of the Middle-Aged Millennial
As an accessibility driver at New York City’s JFK airport, Melissa Jackson spends all day cheerily ushering other people toward the kinds of dream vacations she’ll never experience herself. The protagonist of Hulu’s How to Die Alone is terrified of flying—and even if she wasn’t, Mel can’t imagine scraping together enough money to travel. She has no savings, no real friends, and no romantic prospects. Naturally, she’s also afraid of falling in love.
The new series, which Natasha Rothwell created and stars in, joins shows such as Insecure, Atlanta, Girls, and Broad City in capturing the ennui of a Millennial protagonist who feels stuck in place. But unlike those comedies about feckless 20-somethings, which premiered in the 2010s, How to Die Alone focuses on the arrested adolescence of a Millennial who’s now in her mid-30s, and still not doing much better. (Though Rothwell, who was born in 1980, is technically a young Gen Xer, she plays a 35-year-old on the show.) And as much as Mel might be to blame for aimlessly slogging through adulthood, How to Die Alone also depicts the hurdles that many of us in the new “lost generation” still face as we approach middle age.
By now, the sociopolitical troubles plaguing Millennials are well documented: As my colleague Annie Lowrey wrote in 2021, the “pandemic recession has led not-so-young adults to put off having kids, buying a house, getting married, or investing in a car—yet again.” And in the time since, many either are still playing catch-up or find themselves trapped in a precarious version of the American dream, all while watching the richest people in the country profit from those with limited economic mobility. Mel’s life is undeniably affected by these phenomena, and by the interpersonal trends that have sprung up alongside the economic challenges: Whereas her closest work friend is a rich kid who has a job only to satisfy a trust-fund requirement, she struggles just to afford astronomical living expenses. For her 35th birthday, the best thing Mel can splurge on is a dresser from a European home-goods store that’s meant to stand in for IKEA, a brand that’s come to symbolize Millennial domesticity—even as the products tend to crumble under repeated use, a metaphor in and of itself.
Millennial-focused series have long nodded to the instability faced by a generation of perma-renters: Early in Insecure, for example, a dilapidated couch symbolized the decay in one couple’s relationship, and even after the sofa was replaced, the damage was done. Rothwell, who was the first writer hired on Insecure, rose to fame for playing Kelli, the character most removed from the dysfunction of the main cast. Kelli reliably served as a refreshing contrast to Issa, Insecure’s bumbling protagonist, in part because she seemed to have it together. Issa’s journey followed a common path, taking her closer to self-assurance as she crossed into her 30s, but Kelli—a fun-loving, outspoken accountant—seemed like she was already there from the start.
Mel is a far cry from that confident tax professional. At the start of How to Die Alone, she sounds more like Atlanta’s fretful Princeton dropout, Earn, or one of the anxious miscreants on Girls—despite being several years older than all of those characters. Part of what fuels Mel’s insecurity is the persistent feeling that major milestones are passing her by as she ages, that she should have already figured things out by now—a sentiment that seems to be shared by many other Millennials. At one point, she negatively compares herself to the pop singer Lizzo, whose feel-good anthems captured a certain kind of Instagram-quotable girlboss optimism that became popular in the late Obama era. To Mel, Lizzo’s success at 35 is just another reminder that some people her age have managed to live out the promise of such idealistic visions.
For all her worrying that being 35 makes her too old to achieve some goals, Mel also doesn’t feel like enough of an adult to climb the professional ranks. That, too, is now a common sentiment—and the show’s attention to it marks an interesting pivot from the career dilemmas reflected in previous generations’ pop-culture 30-somethings: Take Frasier Crane, the Kelsey Grammer character who was already an established psychiatrist when he first appeared as a guest on Cheers in 1984. Frasier certainly had career crises, mostly driven by his romantic failures. But as a Harvard-educated Boomer, he never seriously questioned whether he was capable of practicing medicine.
[Read: “Gen Z” only exists in your head]
And it wasn’t just white Ivy League alums who claimed success for themselves as they entered their 30s: In the pilot of Girlfriends, which premiered in 2000, Gen Xer Joan Clayton (Tracee Ellis Ross) was a 29-year-old attorney who not only excelled at her work but also lied about being younger to make the wins seem even more impressive. It’s clear which side of the sellout-DIYer binary she saw herself on, but in today’s economic conditions, most rungs on the corporate ladder simply have fewer benefits to offer. Working long hours at a law firm is no guarantee of affording a mortgage, much less in the historic Central Los Angeles, where Joan was a proud homeowner.
How to Die Alone wrestles with what it even means to try when opportunities for career advancement come few and far between—and how Mel’s professional woes color her relationships with her family, her closest friend, and the ex she regrets leaving. Mel wasn’t born into wealth, but her mother and older brother seem comfortably middle-class, and they’re baffled by Mel resigning herself to a life of five-figure debt. Their frustrations with her don’t come solely from a place of judgment—like most families, they just can’t afford to cover Mel’s expenses indefinitely. Whatever grace they may have extended to her in the past seems to have expired as she edged further into her 30s, a decade when a woman floundering in her love life seems to draw as much condescension as one struggling with work does. The message is clear: Mel needs to get serious—now.
Without spoiling too much, there’s an unlikely shift in their dynamic late in the season—but not because Mel gets a fancy new job. Thankfully, How to Die Alone doesn’t present a management-training program as her ticket to happiness, or even to self-actualization. Instead, the series spends considerable time exploring the unexpected sources of support around Mel, and nudging her to invest in the people who have always seen more in her. Although Mel still finds herself landing in some trouble later on, it’s clear that she’ll benefit from having let those people get closer—even if it means they’re witnessing her messiness up close. The chaos might not be fully resolved, but she finally grows up when she accepts that there’s no virtue in navigating it on her own.