In 2007, when Jai Rodriguez walked into Jayuya Barbershop in Humboldt Park it was his first time getting a haircut he actually wanted.
For years, Rodriguez kept his hair curly and long down his back. The cut he had in mind was drastically shorter — so much so that the barber was nervous about cutting it and asked Rodriguez five times if he was sure, Rodriguez said.
“It took him a while, and I remember the whole barbershop stopped what they were doing to come see,” Rodriguez said. “It was just so affirming to walk out of there and have the haircut that I wanted.”
Now, Rodriguez, a 38-year-old Puerto Rican and transmasculine barber based in south suburban Homewood, wants queer people who sit in his barber chair to feel the same affirmations. Through education and mentorship within his community, Rodriguez is building a barbershop centered around Black, queer, transgender people.
“One of the things that we don’t get all the time is businesses or places that put Black queer trans folks to the front,” Rodriguez said. “I think that when we make a service that’s made for all of us — if you are servicing queer trans Black folks — then everything else can come afterwards.”
For now, Rodriguez cuts hair out of his home. Most clients find him by word of mouth and identify as LGBTQ, he said. He books clients multiple days a week. Some travel by carpool in groups, booking entire afternoons at a time.
Rodriguez is also the host of Boi Talk, a transmasculine support group through Brave Space Alliance, a Black and trans-led LGBTQ center based in Hyde Park at 1515 E. 52nd Place. Two Saturdays a month, he works hair appointments out of Brave Space Alliance, an idea he helped bring to the organization.
For Rodriguez, hair is an essential part of how queer people express themselves. It holds the power to make a statement and “the freedom” to be who you are, he said.
“I was told I would look super manly if I cut off all my hair,” Rodriguez said. “I think before I knew I was trans, I kind of battled with keeping hair for somebody else because it made them feel comfortable. When I was able to chop my hair down to a one — it was so freeing. I was able to look at myself so differently than I used to before.”
Rodriguez grew up in Humboldt Park. Routine visits to Jayuya Barbershop led Rodriguez to the idea of cutting his own hair. He spent hours learning from barbers in neighborhood shops and eventually got a job cutting hair at Jayuya.
Rodriguez later went independent, buying a vintage barber chair from a retiring barber and cutting hair out of his mother’s Humboldt Park home. Rodriguez built a following among queer clients and began cultivating a space where LGBTQ people could be their authentic selves.
“We could be as gay as we wanted to be,” Rodriguez said. “We didn’t have to dial anything down or constantly be monitoring.”
Rodriguez said he is proud to be “visibly queer,” but he noted queerness is not something people can hide or turn off when walking into a barbershop, even if there is an urge to do so.
“Being in a barbershop can also be really weird for somebody who is not a straight dude,” Rodriguez said. “The conversations get really weird really fast. It’s super sexist.”
Rodriguez working out of his own space has allowed for clients to discuss difficult topics, like gender-affirming health care, gender dysphoria, relationships and family. Clients share resources while getting representation and mentorship from Rodriguez. Safety is a top priority, he said.
“I take my job really seriously because there’s not that many people that come in such close contact with you. It’s literally like doctors — and barbers,” Rodriguez said. “I’m a person that is pretty big on personal space, so I really make sure that I’m in the right headspace and in the right energy when I’m dealing with my clients because I know It can get really uncomfortable when someone’s not respecting what you want or what you need at that point.”
Benji Hart, 33, of Woodlawn, said being able to discuss LGBTQ topics with their barber is one of the reasons they keep coming back to Rodriguez.
“It’s great having another queer person of color that not just understands my hair but understands me,” Hart said. “We can talk about what’s going on in our lives, we can talk about relationship advice and friendship advice and navigating these issues of identities with our families.”
Hart has been a client of Rodriguez since 2013. They said they experienced pushback from other barbers in the past and were told certain styles they asked for wouldn’t be what they wanted.
Rodriguez always knew where Hart was coming from. Rodriguez always listened.
“Jai really knows my hair,” Hart said. “Jai is really good at helping you figure out what you want without telling you what you want and really being a guide for you and figuring out the look that was best for you.”
Rodriguez’s said he hopes to open a three-chair barbershop to service queer and trans people by the end of the year. He recently completed a business course through Sunshine Enterprises and is seeking an accessible space on the South Side.
Rodriguez envisions a space where pronouns are respected and where he can teach other queer barbers to build their own clientele.
Rodriguez hopes having his own location will help draw attention to the work he is doing, he said. He wants people to understand there is a need for LGBTQ friendly space within barbershops and a market for queer and trans people who need barbers that listen to them.
“The feeling when you get a good haircut — it’s like you’re on top of the world,” Rodriguez said. “That’s always what I’m looking for: to give people exactly what they want and to know what exactly it means when you get it right.”