[6] In high school, Esposito swam breaststroke on the swim team,[7] was a member of a community service group called The Marians Society,[8] and was a semifinalist for the National Merit Scholarship Program.

[15] After returning to Illinois, Esposito began a Master of Social Work at the University of Chicago for one semester, before dropping out and deciding to pursue a different career.

[12] Esposito began her stand-up career in Chicago, performing in various local venues, including as a regular at The Lincoln Lodge from 2007 to 2011.

Esposito co-hosted the stand-up comedy podcast Put Your Hands Together with River Butcher, which was recorded weekly in front of a live audience at the Upright Citizens Brigade Theater in Los Angeles from 2013 until July 2019.

[24][25] Esposito is known for her lesbian content creation,[26] especially hers and Butcher's television show Take My Wife, which streamed on Seeso until the service was discontinued in November 2017.

[30] Queery guests have included River Butcher, Lena Waithe, Tegan Quin, Sara Quin, Evan Rachel Wood, Jill Soloway, Mary Lambert, Andrea Gibson, Margaret Cho, Alia Shawkat, Roxane Gay, Trixie Mattel, and Lea DeLaria.

The special was free to stream on Esposito's website, but viewers could pay to download a copy and proceeds would benefit RAINN, the United States' largest anti-sexual violence organization.

[39][40][41] Butcher and Esposito collaborated on multiple projects, including the Put Your Hands Together stand-up show, the podcast Wham!