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Photograph: Jen Painter

How to definitely get laid on Halloween

Get tips from Never Sleep Alone host Dr. Alex Schiller as she explains how to up your chances of getting laid on Halloween

Written by
Tolly Wright

It’s not a secret that being single in this city can be difficult: Navigating all the best dating apps for New Yorkers and choosing a first-date restaurant might seem damn near impossible. Luckily, the “sexual psychologist” and author of the dating-advice manual Never Sleep Alone, Dr. Alex Schiller (the alter ego of talented Roslyn Hart, who performs in cabaret shows), is here to explain just what you need to do if you want to hook up this Halloween.

RECOMMENDED: See all Halloween NYC coverage

First things first: What kind of costume should I wear?
One that makes you feel fuckable. And carry a prop that people want to play with. Cleopatra should have a live snake (easily rentable), Indiana Jones should carry a whip, and Christian Grey should have a paddle and wrist cuffs (borrow from me). One year, I went dressed as a slutty Andy Warhol, and everyone I met wanted to fill my soup can.

How can you tell if someone wearing a mask is cute or not?
Don’t worry about looks; worry about chemistry. And masks should stay on during the act, so don’t waste your time on people with masks that cover their mouths unless you’re a masochist.

Can I take candy from a stranger if they’re sexy?
You’re an adult now; buy your own damn candy. Adults want three things on Halloween: attention, alcohol and orgasms. Feel free to take those treats from whomever you want to trick.

What’s the biggest mistake I could make to scare them off before we have the chance to get freaky?
Don't drop character. You are not some unfuckable finance douche who can’t hold his liquor. You are James Bond, Khal Drogo, Johnny from Dirty Dancing—you buy the drinks, you defend her honor and you don’t drop her when you dip her. You are not some awkward, flat-ironed intern holding out for “The One.” You are Helen of Troy, Pocahontas, Marlene Dietrich—you stand up straight, you enjoy the rain and you let him go down on you in the Uber car.

Where should I go to find another randy Halloween reveler?
Everyone wants to get laid on Halloween, so you could probably find a BJ in the back aisle of a bodega. But if you wanna keep it classy, laugh your ass off and sing your heart out with hundreds of horny single people, come to my interactive show and costume party at Joe’s Pub on October 31 at 9:30pm. Warning: If you sit in the front singles section, you will make out with someone.

See the show!

  • Music
  • Cabaret and standards
  • price 2 of 4

Talented character actor and cabaret comic Roslyn Hart plays "sexual psychologist" Dr. Alex Schiller in this interactive bash. The doctor’s goal: getting the audience in the mood with a few choice tunes and making sure all the single people in the audience hook up.

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