Iris May has a lot to say. Her podcast proves the personable Chicagoan has stories, opinions, and strong feelings about pretty much anything — providing motivational messages and poignant dating advice, inspiring her fellow dolls to take life by the horns.
From an orphanage in Bulgaria to later being shipped off to boarding school, May has learned the importance of being grateful for where you are in life. Right now, her preferred destination is a podcast studio, mic in hand, ready to debrief her loyal listeners on whatever the day brought.
Fearlessly honest and refreshingly unfiltered, Iris May is an entertaining queer voice we should all be tuning into. As her popular show “I Have No Idea What I’m Doing” hits its third season, So.Gay chatted with the enthusiastic singer and podcaster. Read our full conversation with the talent below!
So.Gay: I’d love to hear about your queer awakening and your coming-out journey.
Iris May: I’m actually adopted. I’m from Bulgaria. I came to America when I was 19 months old. I always say I didn’t ask for this; I was just born into it. God, or someone up there, gave me this opportunity to live a beautiful life. I think about that a lot. Whenever I’m having a really bad day, I think of the life I could have had. I could have been on the streets in the middle of Bulgaria. It would have been a totally different life, and I wouldn’t be able to be who I am today. I’m not usually the type to say I’ve had it hard, because I think everyone has. But I will say: I was born in the middle of nowhere in Bulgaria, and luckily, two amazing parents, my mom and dad, gave me the life I have now.
I came to Chicago when I was younger and grew up in Northbrook, in the suburbs with humble beginnings. I went to a normal school and always felt different. I would hang out with the boys because I’m kind of a tomboy at heart, to be honest. I love sports. I love hanging out with the boys, but I’ve always felt like one of the girls at heart. I loved being with the boys, but I never felt like I could fully connect. I’d always end up going back to the girls.
When I became who I am, a lot of my girlfriends were like, “We’re not surprised, you were one of the girls from the beginning.” It was a really accepting time for me. I did lose a couple of very good friends, and I’ll get into that later.
I went to elementary school, then I was sent to boarding school because I felt so different, which is a little sad, I know. Honestly, I don’t think I would be here now without that experience. I know that sounds strange, but I’ve always felt it in my gut. Boarding school is not what people think it is, I actually have a whole confessional episode about it. But the bottom line is: I had to grow up really fast. I was sent at 14. I had to learn how to pack my own bags, remember my own toothbrush, and handle everything myself. My parents helped here and there, but within a year I was heading to the airport on my own. I think that’s so young.
I went to boarding school in Connecticut and grew up fast. I would go to New York, have fun, explore, and figure out who I was. This was the era of Gossip Girl, Jersey Shore, Lady Gaga. I remember in 2013, gay rights were being recognized all across the United States, and “We Can’t Stop” by Miley Cyrus was playing everywhere. I was like, ” This is awesome.” It was a really cool time to be in high school, but still really challenging. I didn’t transition then.
So, I reached high school, and I had a really good core group of friends. Luckily, I really wasn’t made fun of. Everybody has their weird times. I was such an artsy kid, and I surrounded myself with artsy kids. I just have these instinctual gut feelings where if I’m not in a good environment, I’m out. I just remove myself from those situations before they get to me. Knock on wood.
I started really finding myself when Katy Perry’s One of the Boys came out. I’m a huge Katy Perry fan, people either love that or hate that. It was a really big album at the time. I always felt like I was one of the boys, but deep down, I always knew I was a woman. The album is called “One of the Boys,” but the whole thing is about wanting to shave her legs, be a girl, and explore who she is. That album really helped me become who I am.
I grew up Jewish and Catholic. I’m not super religious, but I went to a temple and sang in the choir. I always say her story and mine are very similar. I didn’t grow up as strict as she did, but I could relate to feeling like the black sheep, always asking, why is God like this? I’ve always felt like we’re on the same wavelength. She just gets it.
So, back to high school. I hadn’t transitioned yet, but I knew the person I was presenting to the world wasn’t really me. I just wasn’t ready. Fast forward to college. That’s when I was like, okay, let’s put on a wig, let’s put on a heel, let’s do drag. I wanted to be seen. I didn’t care what day it was. I would go out from 11 to 4 in the morning because I knew if there was a camera, I would be on it. That was just the hustle. Back then, I was little Iris May. And there’s a big difference between Iris May and Iris, the person I am today. Iris is calm, collected — she just wants to be normal, get married, have children, give back to the world. And then there’s Iris May, who is everything: a powerhouse singer, a podcaster, an influencer, and an entrepreneur. That’s kind of where I started finding myself, and drag became a part of who I was. I realized: this isn’t a phase. This is who I am. I always say it’s not a decision to be trans. It’s just that I became who I was always meant to be. I made the choice to tell my friends, because when big changes happen in your life, people are either going to be there or they’re not. A lot of the dolls get so scared. I get DMs all the time from girls asking, what do I do? I say, look, regardless of what the change is, whether you move to a different city, get a divorce, have a baby, or transition, some people are going to be there for you and some people are going to bounce. That’s just how life goes. The real ones who stay are the ones who support you. I will say, I did lose some very good friends.
So.Gay: I’m so sorry to hear that.
Iris May: I’ve always weirdly been a lone wolf, and I can stay one. I get emotional talking about it. It’s just kind of in my blood, sadly. But I’m okay with that. Sometimes you have to accept it. Being a lone wolf isn’t a bad thing. It keeps you grounded. I used to be so regretful about losing friends. In your 20s, you’re just like, “Screw you, I hate you.” But then you get to a point where you’re like, “If they come back, they come back. If they don’t, it is what it is.”
Don’t be mad, don’t be spiteful. You’re allowed to have your feelings, but give them grace. Kill them with kindness. I think we should never be envious of our friends, especially women. We should support each other, because women go through so many transitions in life: having a baby, a gender transition, losing a relationship, and changing careers. If you’re there for someone through all of that, you’re either a lifer or you’re not. I lost a couple of friends. It happens. I still care about them. But sometimes when people leave, it’s actually a good thing. Do you really want them in your life if they’re going to leave the moment things get hard? They showed you who they are. They made it easier for you. You get older, and you just don’t have time for it. That’s something you have to remind yourself when you’re going through something extremely hard: I have a roof over my head, I have people who love me, and I’m breathing. That’s what counts. I always say: God wouldn’t give you a challenge you weren’t meant to get through. That’s something I’ve told myself throughout my Saturn return from 27 to 30. Tears, blood, sweat… you’re going to get through it.
So.Gay: How did your song featuring Carole Baskin from “Tiger King” come about?
Iris May: I worked with Carole Baskin, and honestly, that’s what got me big. I just started DMing her and commenting over and over, just to be persistent. Eventually she DMed me back. It was wild. It was about a year after Tiger King, and I’m sitting in my apartment with my friend when she sends me her number. A year after Tiger King and she was still trending. I sent her a demo and said, if you want to be in it, it’s a great song. Then I get a FaceTime from her and I’m like, “What the hell, Carole Baskin is FaceTiming me.” She was so nice. She said, “I would love to be in your music video,” and she did it for free, which made it even cooler. I was like, all right, there’s my career. I thought I was going to skyrocket. Unfortunately, it dropped at the tail end of COVID. The timing just wasn’t right, and the marketing wasn’t there either. It didn’t quite land, but people saw me and took notice. I think it would have been much bigger without COVID. After that, I kind of stepped away from music. One day I want to come back to it, but right now I’m focused on myself and carving out space in this new media world.
So.Gay: How did transitioning give you the confidence to live your best life?
Iris May: I wrote a song called “For Myself.” I get emotional talking about it because I’m just an emotional girl. The meaning is hidden in the lyrics. I wrote it about four and a half years ago, right before I transitioned, when I was finally coming to terms with who I was. I wrote it entirely for myself. I’m going to do this for me, not for anybody else. That’s a really big thing. Going back to my Saturn return, you start to realize you’re not doing this for others anymore. In your 20s, you just want to be seen, validated, and loved by everyone. I just ripped off the band-aid: I’m done doing it for others. I’m going to do it for myself, authentically. So I wrote that song. Basically, transitioning meant giving up my teenage dream. I had to let go of the idea of getting married as someone I wasn’t. I had to release this version of myself I’d been holding onto forever. Then I became who I truly was.
So.Gay: As that person now, are you feeling more empowered than ever?
Iris May: I am her. I am Iris. I am beautiful. I have not looked back, and I can’t look back. I mean, there are days where I’m like, “Man, it would just be so great to be a man for one day.” But then I’m like, “No, please, don’t bring me back to that life.” That’s just a joke women make. This next season on the podcast, I actually cried on camera, and I’ve never done that before. I opened up about a really big breakup that just broke me. I think that’s important to show, because I don’t usually talk about that side of things. Next season is a lot more emotional and a lot more honest.
So.Gay: Do you have any advice for how cis gay men, who make up a large part of our readership, can be better allies to Trans women and the broader community?
Iris May: I think a lot of gay men, unfortunately, right now, are really mean to other gay guys. How can you judge someone when you’ve been judged your whole life? This is supposed to be a place where everyone feels safe and welcomed, because we’ve had to fight for our lives to be ourselves to get to this spot. The fact that we can’t walk into a bar and be our authentic selves is really sad. I will call it out when I see it, because I think it’s sad. I’m like, “Why do you even care?” I mean, there are times when people overstep boundaries and are inappropriate. That’s when you say, “Hey, I’m not interested,” and you don’t need to be a dick about it. I deal with straight men every single day who say things like that. It’s just weird.
So.Gay: Do you have any advice for the next generation?
Iris May: Accept what you’re feeling. Whatever it is, embrace it. If you’re sad, sit with it. If you’re happy, lean into it. That’s what I would say to the next generation, because once you stop fighting your own emotions, you will feel so much better. I say this because sometimes we’re all in denial of what we’re actually feeling. We get so anxious. You know what? It happens. You’re allowed to have your feelings, of course. But I think you have to accept that feeling. Okay, you’re mad. So be mad. That’s something I learned in therapy. I never wanted to be angry. My therapist would say, be mad, you’re upset, you’re allowed to be upset. I’d say, yeah, but it makes me so uncomfortable. She’d go, yeah, but that’s an emotion, that’s a feeling. You’re allowed to feel that.
So.Gay: In the spirit of that, is there anything you’re upset by that you think the world needs to take a closer look at?
Iris May: Yes, oh my God, I’m about to go off. I’m so pissed that Trans women can be so vicious towards girls who are earlier in their transition. Look, I felt so ugly before I transitioned. There’s always that awkward phase. Filler helps, surgery helps. But some people don’t have access to those things. Everyone’s transition is different. Take your time. That’s what I would say. Why are you judging them when you were in the same spot, girl? It’s like puberty for girls. We all go through it. So I think that’s something we gotta be better about: not being so judgmental towards the dolls, because we’re already so vulnerable. But that’s a woman thing. Women are always judging each other.
So.Gay: And I hear you’re making new music?
Iris May: I think I’m ready to start a new chapter. It has nothing to do with the podcast, it’s purely music. We’re going to work on a record and make something really good. That “Since U Been Gone” kind of energy. It’s going to be everything. I want to bring back that feeling of being young as a millennial: CD player in the back of the car, mom’s driving, music blasting. I want to feel like I’m listening to Hilary Duff. I want to bring back hits like “Breakaway,” that Alanis Morissette energy, that band sound. That nostalgic feeling of being a teen pop girly.
So.Gay: Maybe people will have Iris May posters in their room.
Iris May: That would be great. You know who else deserves a poster and is a huge inspiration for me? My mom. Really, all the women in my life from my mom to my girlfriends. I learn from them. They teach me, they love me, they push me, and I love that. I also have to bring up the Pussycat Dolls. They are honestly the reason I’m convinced I transitioned. When I was in fifth grade, probably way too young, I saw femininity, and I was like, “I want to be her.” She embodied everything a woman is to me: looks, confidence, power, sexiness. Nicole Scherzinger to me was just… I don’t know how to describe it. I’m a huge fan of that era. Early 2000s, women were just iconic. They were hot. I try to channel them in my music and podcast.
