Halloween Love Tricks

Want to scare up some dates? This holiday’s packed with opportunities to make sparks fly with strangers. Here’s some advice that’ll score you a bagful of phone numbers.

By Dustin Goot

hat holiday crosses the romantic anonymity of a masquerade ball with the party-hard attitude of New Year’s Eve? Halloween, of course, which is well on its way to being the single person’s favorite night of the year! This uninhibited evening always serves up dozens of flirtation opportunities, whether that’s at a friend’s Halloween party, a local parade, or a costume ball at a bar. If finding love is on your agenda, consider these tips from experts and Halloween pickup veterans.

Use your costume to turn heads
Your costume, of course, can be an immediate icebreaker—so go ahead and be as crazy and outrageous as you can muster. Colleen, a rowing coach in Boston, remembers
People in costume are often dying to act out their disguise.
dressing up with friends as a nudist colony: “We wore skin-toned leotards and those crazy plastic boobs they sell.” “We were all very popular that night,” she says. “I talked to a ton of cute guys.” Even if you’re not that adventurous or only have time to pick up a store-bought ensemble, find a way to give it a personal touch. In deciding what to be, “relate it to someone or something you admire,” suggests Jill Spiegel, author of The Flirtologist’s Guide to Dating. “If you love race cars, dress up as a driver; if you love art, be Andy Warhol.” The more you reveal of yourself, the stronger connection you can make with others.

Roll with the role play
People in costume are often dying to act out their disguise; indulge them and you’re bound to bond. Eric, a real-estate agent in Chicago, recalls meeting a woman in a silver-sequined tank top and jeans who introduced herself at “Penny Lane” (the groupie character from Almost Famous). “When I asked her real name, she acted exasperated and said ‘Kate Hudson,’” he says. Even though he eventually found out her name was Shelly, they continued with this playful charade and things went so well she gave him her number — signed as “Kate” — and the twosome ended up dating.

Entice sweets with sweets
Candy giving is a beloved part of the Halloween ritual, and it can also be a great entrée into conversations with strangers, says Spiegel. Bring a bag of candy and playfully offer it to other party goers; make them say “Trick or treat?” first. Alternatively, suggests Spiegel, “You can bring your favorite candy from childhood and ask the other person what his or her favorite is.” This will initiate a more personal conversation that’s rife with nostalgic, feel-good vibes that are bound to rub off on you.

Make it a group thing
Coordinate costumes with friends and you will make an even bigger impression at a party, advises Lance Mason, founder of “I’ve gone with a bunch of guys
It’s a great way to get a conversation flowing.
dressed as Elvis,” Mason says. “It creates this social circle around you that people want to be a part of.” Some other ideas: Dorothy et al from The Wizard Of Oz, an entire baseball team, or a sultan and his belly dancers. No matter what the idea, it will express that you’re someone who’s friendly and approachable, which sure beats people wondering “So who is that lone stranger in the corner dressed up as a mummy?”

Delve into people’s Halloween pasts
Pretty much everyone has had some pretty vivid memories about Halloween. So if you’d like to see someone’s eyes light up, ask him or her, “What’s the best Halloween costume you ever wore?” or “So when you were a kid, did you ever toilet paper your neighbor’s house? Come on, you can be honest, I won’t tell anyone…” Turning the conversation toward scary topics can also liven up a typical conversation, whether that’s “Do you believe in ghosts?” or “Hey, I’m taking a poll and want to know who you think is scarier: Freddy Krueger from Nightmare On Elm Street or Jason from Friday the 13th?” It’s a great way to get a conversation flowing on the 31st without any awkwardness, so go for it.

Dustin Goot is a freelance writer based in New York City. He has also written on dating and relationships for Wired and Time Out New York.
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