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Dating Triumphs and Tragedies
by Nicole Roberge

Trick or Treating - Halloween Romance

Whether you’re handing out candy to trick-or-treaters, or getting dressed as Martinis with your friends to go to a bash, Halloween is a time to cleverly meet potential daters. Costumes, candy and cocktails all help to lighten the mood a bit and push you in the direction of maybe Mr. Right…or Frankenstein.

Halloween parties are of course an opportunity to meet people, but it can be tricky depending on costume. Some costumes are more dependent on clothing, such as Superman, where you can see the whole package, but someone like Spiderman is more tricky because his face is covered. So there’s a little mystery there. Which can be fun, but also, you’re not really sure what you’re getting. But that can also be a good thing, because if you do strike up conversation and hit it off, it’s better that you two connect. And what a fun story it will be to tell people about that time you were She-rah and got a little tipsy and Spiderman caught you and it was love at first fall. True romance.


If you’re at a bar, typical bar rules apply, though it will of course be a little more chaotic given the Halloween themes and people dressed as anything from Skeletor to Derek Jeter, but it’s still a good setting to meet people. The environment and ability to move around from one group to the next makes it easy, and the fun atmosphere of the night makes it a little more lighthearted than your typical bar night. Also, the fact that you’re in costume makes it exciting. Being dressed up gives you that sense of not really being yourself, so you feel a little more adventurous. Perhaps you and your friends are the cast of Desperate Housewives? Well, get into character!

There are other Halloween events besides dressing up and drinking, so don’t feel as if those are the only options. Check your local newspaper or search online. Some towns hold events leading up to Halloween, or the night of. There are plenty of Fall Festivities and Halloween-oriented events, such as parades, pumpkin patches, Fall Festivals, Hayrides, Fairs and Haunted Houses—all of which are good and festive and can be a fun atmosphere for meeting people.

The art of Trick-Or-Treating has many aspects to it that can provide you with man meeting material. First, there is the candy aisle. If there is a single guy who is handing out candy to little ones, which is sweet, clearly, he’ll be buying it last minute—on Halloween. So if you’re going to be buying candy to hand out, do it the same. Mosey through the candy aisle, perusing your choices, and wait for Mr. Goodbar to come along. Then give him suggestions about what you’ve noticed kids to like best, and then what they don’t like so that he can have the leftovers.

Then there is the actual Trick-Or-Treating. If you are manning the door, you get to see everyone who comes by. A nice, single Dad? Studly Uncle? Older brother? Whatever the case, strike up conversation. Maybe he’s a neighbor you’ve never met. Don’t just toss some candy into a pumpkin bucket and let the kids be on their way. A simple smile with your “Happy Halloween” can go a long way.

If you’re taking kids out Trick-Or-Treating, it’s the same thing. Now, if you’re real ambitious, you could plot your route towards Bachelor Pad City, but remember, this is for the kids. Still, if the guy is seemingly single, don’t take the candy and run. Chat it up, ask why he isn’t trick-or-treating, or where his costume is. Chances are, he’s probably a little tired of getting off the couch every five seconds to open the door and throw some candy in a bag. He’ll welcome the conversation…and the cute girl.

Whereas Halloween used to just be about the candy, now it’s about the eye-candy, and what may come of it. Fall is a great time to meet people and establish relationships. Halloween is one of those holidays that is fun and festive and you can just kind of be a little more risky and “not yourself.” So you may meet him, but whether he’s a trick or a treat is uncertain. So if it all fails…at least the next day, Halloween candy is on sale.

Dating Triumphs and Tragedies is published every Sunday by Online Dating Magazine columnist Nicole Roberge. She can be reached at

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