Irl: Singles Mixer

Two queer musicians, one intimate night underground. Brooklyn's Your Friend Rachel brings her distinctive sound to Dorothy's subterranean stage, sharing the bill with Chicago's The God Awful Small Affairs. Live music for people who actually listen — expect the kind of performance that reminds you why you showed up in the first place.

A fun and flirty show built for queers finding their people later in life. If you're looking to make real connections with other late bloomers in the community, this is your night — expect good energy, genuine conversations, and the kind of vibe where everyone's actually here for the same reason.

Rhinestone Microphone is a monthly queer open mic celebrating all forms of performance — 10 local performers get five minutes to share what they do best in front of an enthusiastic crowd, with priority given to BIPOC and first-time performers. The night opens with open mic and closes with award-winning burlesque performer Harlem Nyte. Doors at 6pm, show starts at 7pm. $8 in advance, $12 at the door.

Jenny Fox, Chicago's Puerto Rican Princess, takes over Dorothy's basement for a night of pure perreo, cumbiatón, salsa, merengue, and más. Doors at 6pm, Jenny spins from 9pm to 1am—come ready to dance and romperla. $10 cover at the door; Dorothy stays open until 2am.

The Bi Wives Club is back at Dorothy with a stacked lineup of queer comics who actually know how to land a joke. Amy Geist, Luis Arevalo, Lizzie Kaniecki, Anna P. Nannicelli, and the three producers behind the show—Kris Lantzy, Kayla McCaffrey, and Christen Manville—bring playful, authentic humor to a room that gets it. ASL interpretation included. $12 in advance, $17 at the door. Show starts at 7pm; Dorothy opens at 6pm.

Monday nights at Dorothy just got a musical upgrade. Sapphic Serenade kicks off with Monday Musicals Power Hour (7-8pm) — belt out your favorite Broadway tunes before the full karaoke floor opens until last call. Free karaoke, enthusiastic queers, and the best cocktails in town. Sign-ups start at 6pm; 21+ with valid ID.