By Thomas Whitfield

Happy Halloween! Now everyone, take your clothing off! I worked as a bartender for almost 15 years, and I saw more skin working Halloween night than any night at a strip club. The gays love a good costume that shows off their bodies, and why shouldn’t they? They’ve worked hard for them. But, the creativity is sometimes lacking. I mean, how many shirtless superheroes can there really be? Someone give me sexy John Wayne Gacy, am I right?

Last Halloween, I feel in love… with a vampire. I was at an apartment party on 18th Street in Chelsea when this beautiful guy showed up: blue eyes, jet black hair and dressed like that Twilight guy. He was in character the entire night. I ended up getting messed up, and we eventually f*cked in the stairwell (real classy, I know). He disappeared after, and I haven’t seen him since. I asked a few people about him, but it was packed, and no one seemed to know. It was the hottest sex, and I can’t stop thinking about him. This isn’t as much a question as it’s me hoping you’ll print this and he’ll come looking for me. Dramatic? Tragic? Pathetic? – Male, Gay, 23

There you go. I’m putting it out into the universe. I don’t know if this is dramatic, tragic, pathetic, weird or maybe fun? Might be a fetish, an attraction to vampires? Are you a certified fang banger? Seriously though, this might be something you want to explore, just in case this guy doesn’t come flying back around. Fingers crossed you meet him again this year, but maybe try to get his contact info too, instead of just his vampire D.

I’ve been struggling with my gender identity for a while. I think I might actually be a woman. I’ve felt this way for a really long time, but always hid it and thought maybe I was just gay. I guess I identify as bi though? Lots of questioning going on. As a little kid I remember telling my mom that I was her little girl, not boy, and she would yell at me. Eventually I stopped. I was thinking that maybe this year for Halloween I’d go out in public wearing women’s clothing for the first time and just tell my friends it’s a joke. Test the waters? Is this a terrible idea? Or totally offensive? I’m really scared, but also really excited. – Trans?, Bi, 21

I say go for it. Allow yourself to really dive in and see how you feel. Remember, though, being trans isn’t about just dressing up and going out for a night; it’s more complicated. I’d recommend you check out some online forums and get acquainted with the trans community in NYC. Luckily there are tons of people here who know what you’re going through and can help you make the best decisions for yourself. I think it’s awesome that you want to explore and express this side of yourself, and even though it’s just one night, I hope you have an amazing time!


Sex/Love/Relationship advice? Send your questions to: Instagram: @ThomasWhitfield84