He is known for having co-founded the website The Toast, and written the books Texts from Jane Eyre (2014), The Merry Spinster (2018), Something That May Shock and Discredit You (2020), and Women's Hotel (2024).

[11][12] Lavery has credited the work of Shirley Jackson and her novel We Have Always Lived in the Castle, in particular, and John Bunyan's The Pilgrim's Progress as influential.

[22] The book was based on a column that he wrote first at The Hairpin, then continued at The Toast,[14] which imagines well-known literary characters exchanging text messages.

[24] A short story collection, The Merry Spinster: Tales of Everyday Horror (Henry Holt, 2018), appeared in 2018.

[27][28][29][30] The Merry Spinster reinvents fairy tales such as Cinderella and Beauty and the Beast; in the Los Angeles Times, Agatha French described his renderings as making the "stories both weirder and yet somehow more familiar".

[13] Lavery's third book, a memoir entitled Something That May Shock and Discredit You, was published in February 2020 by Simon & Schuster.

Berkeley[36][37] and "the most followed transgender scholar in the world on social media" including Twitter and Instagram,[38] announced their intention to marry.