In Bachelorette, three unhappy friends show up not-quite-invited to their high school classmate’s swank hotel suite on the eve of her wedding and promptly use it as a venue for their every toxic whim. After comparing notes on their disappointing careers, failed relationships, and uncertain futures, the women embark on a woozy all-nighter of champagne guzzling, coke binges, and reckless deviance. This evening of venom and indulgence provides the backdrop for Leslye Headland’s investigation of gluttony in a contemporary context. Bachelorette is a part of Headland’s Seven Deadly Sins play cycle, an ambitious series exploring the intersection of ancient vices and modern youth.
Headland’s inspiration for using this particular intersection of transgression and culture came at her sister’s wedding, as person after person asked whether she was sad to not be the one getting married. These questions quickly lead Headland to identify a friend’s looming wedding, an emotionally fraught rite of passage for many single women in their late twenties, as the ideal locale to explore generational angst and insecurities. “Where are women most self-pitying? Other people's weddings,” says Headland. “That’s probably the height of women’s self-pity—when one person is being celebrated and moving into adulthood, and everyone else is just miserable.”
Bachelorette dissects that messy transition to adulthood, when juvenile hedonism yields to self-destructive excess. “It’s a play about the in-between space,” says Headland. “The place you are when you're reconciling who you thought you were gonna be when you grew up with who you've actually become.” The anxieties of the Bachelorette’s disaffected ensemble may manifest as raucous debauchery, but for all the giddy fun of id unleashed, Headland skillfully evades a superficial riff on mean girls gone wild and instead delivers a brutally honest portrait of a generation grappling with its fleeting youth.