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But after that, I was like “Nope, this isn’t for me.”
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Once I got to college and actually had friends, I felt more comfortable. We knocked on the door and this girl, Hope Hanley, who was my grade, opened it, and she was like “Terry? And I went with Claire who was eight years old and who dressed up as a princess. That was when kids started staying home or hanging out with their friends. It was just a little too late in my career - I was 12 years old. And one year I went as my same old Dracula. O’CONNOR: I never really had anyone to go trick or treating with, so I would always go with my little sister who is four years younger than me. I also didn’t have friends in high school. SKINNER: Do you think it had something to do with the fact that you were at an all-boys school? I felt comfortable because all my girls were also going hard, and I would help them with their costumes. It wasn’t until college that I became really into doing Halloween. I know how it goes.” And then I just stuck with that. So as a kid, I would always go as a vampire because I was like “I’ve done this once.
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I was so scared of my costumes like marking me as gay, and I didn’t know how to make good straight references.
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O’CONNOR: It’s so funny because I had the opposite response to growing up. I felt so confident that whole day and I always tell people: the first time you go really hard you’ll never go back, because you realize how fun Halloween can be when you allow yourself to give the drama. I was going to go into school and my mom was like “Are you sure?,” and I was like “Bitch yes I’m sure. I had the big Johnny Depp white glasses and a bob. I distinctly remember fifth grade was one of the first times I went really hard for Halloween. It was the only time of the year I could tiptoe into being myself without getting caught in the closet. SKINNER: You’ve definitely heard this many times, but Halloween was always very important to me. On the eve of Halloween 2021, the two spoke about their decision to dress up as Jackie Kennedy and Marilyn Monroe this year, and how Halloween as a holiday has proved to be a pivotal factor in accepting their respective queer identities. Before the two even met, there was an almost cosmic correlation to their costume decisions (In their senior year of high school, Skinner was the Pope and O’Connor a nun.) Now, as a couple, the two have tackled outfits from mega-celebrities Kendall and Kylie Jenner to ice cream moguls like Ben and Jerry, and regularly push the envelope on how to properly curate a Halloween costume. You’d be hard-pressed to find anyone who does Halloween quite like Benito Skinner – more famously known as Benny Drama, the comedic, YouTube sensation– and his boyfriend, the director Terry O’Connor. Benito Skinner as Marilyn Monroe and Terrence O’Connor as Jackie Kennedy.