Through her ongoing advice column “Ask Polly,” collected in the 2016 book How to Be a Person in the World, Heather Havrilesky offers advice on love and life to millennials. Havrilesky studied psychology at Duke University and graduated in 1992. She began her career in online journalism as a columnist for Suck.com from 1996 to 2001; there she co-created the comic strip Filler under the whimsical pseudonym Polly Esther, a name she would later re-use for her advice column “Ask Polly.” She then became a TV critic and writer for Salon.com beginning in 2003. She wrote her first memoir, Disaster Preparedness, in 2011, using the strange coping mechanisms she created in childhood as a jumping-off point for talking about her family and the lessons she learned on the way to adulthood. In 2012 she began writing “Ask Polly,” first for The Awl and then for New York Magazine’s The Cut in 2014. The advice column was unusual for Havrilesky’s blend of long, essay-style answers, frequent use of all caps, and willingness to share her own painful experiences to reassure advice-seekers that they are not alone. In April of 2021, she moved “Ask Polly” to Substack, where as of 2024 it had more than 100,000 free subscribers and thousands of paid subscribers. In 2018, she published her third book, exploring the relationship between the constant belief in something better that is just out of reach and unhappiness in today’s society, entitled What If This Were Enough? In 2022 she published Foreverland: On the Divine Tedium of Marriage, a memoir addressing her sixteen-year marriage and views on love in general.