“When you grow up in a bubble, you don’t see outside that bubble. But once you take a look outside, or you’re forced to take a look outside for whatever reason…it might be jarring at first, but then it’s like wait a minute…That makes so much more sense. Now the bubble just seems like a prison that you’ve been put in.”

Ari Winkler was born to an Orthodox Jewish family in Borough Park, Brooklyn, the fourth out of five siblings. Growing up Orthodox means strict adherence to binary gender separation. He did not talk to a girl who he wasn’t related to until the summer after his senior year of high school. He says he didn’t touch a girl until he was 19.

Today, Ari is forty years old and identifies as queer, but getting to that place was a journey. “When I was young, I didn’t really relate to the other kids,” Ari said. “I never liked what everybody else liked. I never felt like I was part of a group. So, I guess being queer wasn’t that big of a stretch, but it took time, you know?”

I asked Ari if he had any exposure to an openly gay or queer person during his childhood. “Not happy exposure,” Ari replied. “I was sexually molested as a child, but I wouldn’t consider that person queer as much as a sexual predator.” Ari’s only real notion of the queer world came from the stereotypes he saw on television depicting “friendly gay people.”

Ari attended an all-boys Jewish high school. There were only 40 students in his entire class. “We didn’t have the gay guy, the butch lesbian, the goth chick…We didn’t have anything like that.”

Despite receiving zero sex ed and being surrounded by many who believed that gay people are sinners, Ari thinks fondly of his high school experience. “Going through puberty and all that, if I had to see girls every day, I wouldn’t have been able to grow up. It just would have been so much pressure, you know?”

His school days typically lasted 12 hours in order to fit in the complete secular curriculum in addition to the complete Hebrew education. Twice a week he had breakfast, lunch and dinner all at school. He gained a reputation as a rebel, in part because he wore brown shoes even though black shoes were required. He recalls one day when, during a math test, his teacher pulled a cheat-sheet out from under his desk. “He’s like, ‘What are you doing?!’ I said, ‘That was in there! Look at my test, I’m not cheating!’ He’s like, ‘No, you’re cheating. I’m taking you straight to the principal.’ He takes me to the principal, who looks right at the math teacher and goes, ‘You didn’t catch him cheating.’ The math teacher looks at him, astonished. He looks right at my math teacher and says, ‘Ari doesn’t cheat, because Ari doesn’t care.’”

Shortly after graduating high school, Ari got into a ski accident that left him in a coma for 9 days and in the hospital for several months. A year later, Ari attempted suicide, which is tragically common among people who have suffered a traumatic brain injury.

“I kind of get – and I joke about this with my mom – a free pass. They’re like, ‘He’s alive, he can do whatever he wants.’”

Prior to the ski accident, he met the woman who is now his ex-wife. Some of her friends were dating some of his friends and everyone was hanging out. “She had a reputation of being an ice queen,” Ari said. He was admittedly a bit shy around women. They didn’t really say anything to each other.

“But then after the accident, especially for those first few months, I wasn’t intimidated by anything,” Ari explained. “I had no inhibitions. I was just passing by her and her friends, I was like, ‘Hey,’ and she started laughing. And I said, ‘What’s so funny?’ She goes, ‘I don’t know, last I heard you were dead.’ I was like, ‘Well, I’m not dead.’”

The two became friends with an “overriding sexual/emotional tension.” For years they were phone buddies. “Every time we actually got together something would go terribly wrong because there was all this tension.”

During this time – his early twenties – Ari was finally able to explore life outside of Borough Park. He started doing standup in the west village. He developed a coke addiction. He recorded a music album.

He started dating his ex-wife and they got married shortly after. The marriage lasted two years. “We were super in love with each other which, by the way, is a terrible reason to get married.”

A good reason to get married? “You have mutual life goals and you’re not really interested in having fun anymore, and you want to get a partnership going. Love? Love’s a terrible reason to get married. Love’s a good reason to see where it goes.”

For Ari and his ex-wife, love wasn’t enough, mainly because Ari realized he didn’t want to be in a monogamous relationship. He was also experiencing what he calls cock-lust, and fantasies about trans women. When they separated, they cited religious differences as the reason, but internally, they both knew that the main source of the rift was that Ari never wanted to be married in the first place.

Ari doesn’t think his family was that surprised by the divorce. “I think they knew in the back of their heads that it was never going to work out,” Ari said. “With my family it was like, ‘OK, we’re going to go along with this, this is the only chance he’ll ever be normal, but really, good luck, you know?’”

Getting divorced helped Ari realize that he didn’t want to be in that kind of relationship. Now, he could be honest with people from the start. He describes himself on dating profiles as a relationship anarchist.

A couple of years ago, an ex-girlfriend introduced Ari to a new term: queer. “On our first date, she said to me, ‘I’m queer and I don’t do monogamy.’ I was like, ‘I don’t do monogamy either, what’s queer exactly?’ She told me that queer is basically anything that’s not flat-out straight or flat-out gay. Anywhere in the middle is queer. I’m like ‘Oh, wow.’ I’m obviously there, you know? That makes sense.”

Today, Ari still lives in Borough Park, which to this day is still an extremely religious neighborhood. Everything is closed on Friday nights and Saturdays. He is working on selling his home so he can move to Williamsburg and be closer to nightlife and culture.

“Showing my house, I get a lot of seedy guys,” Ari said. “And it’s funny because one in ten will find a way to put their hand on my shoulder and say, ‘Hey, you’re a very good-looking guy.’ I think it’s probably because they’ve had pent up feelings for a while, and I wear nail polish so I’m not going to judge. This way, they can flirt for a second. I just prefer that if they’re going to make an actual pass at me that they shave their face and clean up. I’m like, ‘Am I worth nothing?!’”

Ari remains extremely close with his family, despite not sharing their beliefs. His four siblings are all religious and are married with children. He has 27 nieces and nephews.

Ari considers himself lucky for never having to choose between his family and his freedom. He knows others from the Orthodox community who haven’t been as fortunate. “My family values family above everything else,” Ari explained. “Religion is extremely important to them, but family is even more important than that. So, they may not admit it out loud, because that would be sacrilegious, but it’s true.”

It doesn’t end well when people feel confined, when they have to choose between the love of their family and being true to who they are. “No,” Ari concurred. “You’re either going to end up losing the person, or they’re just going to become dick-holes.”