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Spook-tacular Halloween Dates

If you’re gay and are wondering what to do on the 31st? Here are some ideas for fun nights out—without any frights.

By Dave Singleton

“I love Halloween. I think it should be monthly,” says Atlanta resident Tad, 34. “It’s definitely a gay holiday, so why shouldn’t it be a hot date night, too?”

Tad’s right. Not only is Halloween the biggest growing holiday industry in the U.S., but also it’s a gay celebration (of sorts) that's growing in popularity. We love Halloween for lots of reasons;
Keep in mind that big parades can backfire, romance-wise.
colorful parties, acting like a kid again, and wearing masks. God knows, most gays and lesbians know all about wearing masks, since so many of us have had to hide our gayness at some point.

Halloween is also about taking risks, letting go of inhibitions, and allowing new sides of your personality to emerge. That sounds like a great date, doesn’t it? Before you finalize your plans, consider this advice from daters like you on how to make the night a success, not a scare-fest:

When it comes to costumes: think sexy, not elaborate
This strategy worked well for Rick, Lisa and Andrew.

“I’m an accountant and wanted to shake up my laid-back image a bit, so I went as Superman to show my sexy, flirty side,” says Washingtonian Rick, 35.

“I dressed up as a French maid, which, since I am sort of butch, worked well,” says Orlando native Lisa, 33. “It made my new girlfriend see me as willing to take risks.”

“Since The Pirates of the Caribbean films have been so popular, I dressed up like a pirate,” says Virginian Andrew, 27. “I could move easily in the black pants and loose white shirt, and lose the eye patch later in the evening when I wanted to lock eyes with someone.”

But Halloween daters take note! Beware the overly-involved, unsexy costume! “I dressed up like a courtier from the palace of Marie Antoinette,” says Washingtonian Linda, 30. I thought squeezing into layers of ruffles and makeup would be hot, but I was wrong! How did those randy 18th-century party girls manage romance dressed like that? It sure didn’t work for me!”

Party hearty, but don’t let your date get lost in the ghoulish shuffle
“Big parties can become intimate nights out on the town if you plan them right,” says New
Make sure your costume has a bit of sex appeal.
Yorker Jerry, 35, who never misses the downtown Halloween Parade. This year, he’s taking the man he’s been seeing for four weeks. They’re going as Superman and Aquaman. “Planning the night brought out a playful side in both of us. If nothing else, we’ll laugh and bond as superheroes fighting the crowds,” says Jerry.

But big events can backfire and leave you holding an empty trick-or-treat bag if you aren’t careful. “Being ignored by your date at a big Halloween party sucks, and not in than exciting vampire-style way” says Ken, 34, from New Jersey. “This Halloween, I’m taking my new boyfriend to a big party, but I’ve already made plans for the two of us to be alone afterwards.”

Hide from the creatures of the night in the comfort of your own home
You don’t have to go out to enjoy a Halloween date. “I loved staying in with my new girlfriend to watch The Hunger,” says North Carolinian Ann, 35. “Catherine Deneuve playing a sexy, icy vampire who seduces Susan Sarandon? Perfection! Grabbing my girlfriend’s arm during the scary moments beat trick or treating any night.”

Virginian Chris, 27, agrees. “One of my best dates ever was Halloween last year with the guy I am still seeing. It was one of our first dates and the plan was to watch a DVD at his place. He decorated his place with cobwebs and lit orange candles everywhere and rented two scary movies, Halloween and Carrie. It was a blast.”

If you aren’t already dating Mr. or Ms. Right, a Halloween party can be a great place to meet a date
It certainly was for me. At a party a few years ago, while wearing a Venetian feather mask with black tie, I met a guy dressed as Darth Vader. I had no idea if he was a date prospect. But he was smart, playful, and we talked for a couple of hours, both of us behind our masks.

In retrospect, not seeing each other’s faces was a safe way to flirt. As the evening wore on, we learned a lot about each other. Halloween is freeing in that way; sometimes when you put on a real mask, you take off the invisible one you wear everyday. Our real masks finally came off and my Darth Vader turned out to be a handsome, charming lawyer about my age. We left the party for dinner (which we counted as our first date) and things took off from there. The force was definitely with me that Halloween. May it be with you this one.


Dave Singleton, an award-winning writer and columnist for Match.com since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at davesingleton.writer@gmail.com.
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