Dani Okon, NYLON's associate creative director of video, sat down with her great-aunt, May Okon, to talk about their shared experiences—despite vastly different time frames—living as queer women in New York City. Prior to retirement, May was a journalist for the New York Daily News, having first entered the male-dominated workforce when "the boys were all at war." And, of course, she absolutely killed it. Her only regret? "Retiring at 55," she tells Dani, joking, "Who the hell knew I was gonna live to 100?"

Upon retiring, she moved out to the Hamptons with her partner and bought a home. If she had to do it all over, May says "there are a lot of things I wouldn't do," but she still considers herself "one of the luckiest kids on the face of the earth." Get to know May in the video, above.

Check out the other videos in our series where we placed queer people from different generations in conversation with one another:

Rob Smith and Eddie Jarrel JonesLauren Morelli and GarciaMarlene Colburn and Naima GreenAshlee Marie Preston and Devan Diaz

Produced by: Alexandra Hsie

Camera: Gretta Wilson + Katie Sadler

Edited by: Madeline Stedman