Since its very inception, Halloween has been ridiculously awesome. When you’re young, you get your rad little Batman costume and a sackful of candy, much of which is free of razor blades.

When you’re older, well, let’s just say the treats come in a different form: women dressed as sexy schoolgirls, sexy French maids, sexy Disney princesses and anything else involving tiny tops, short skirts, silk stockings and high heels.

Of course, to win over those costumed cuties, you need to bring your A-game, beginning with a killer costume. And, unless you’re Colin Farrell, no going as yourself. It’s all about creativity, craftiness and confidence. The following four conversation starters will make you the most popular guy at the party… and the one going home with the tastiest (eye) candy.


1. Boxed Wine

Make it: Construct a life-size Franzia box. Duct tape a real wine box on the inside, with a spout at the front in the general vicinity of your man-parts.

Why it works: You’ll have women going down for refills and topping off their refreshments all night long. You’ll also never need to wait for a drink.

How to use it: Keep a stash of plastic wine glasses inside the costume. Approach any woman in line for drinks, bust out the glasses and insist—preferably with some sort of British or French accent—that she join you for a glass of red. You’ll be the toast of the town.


2. Giant Baby

Make it: This one’s simple: a bottle, pacifier and giant diaper are all you need. Being in pretty good shape is highly recommended.

Why it works: Every woman will want her photo taken with you the entire night. It’s also axiomatic that Giant Babies are totally unpunchable, meaning you can get away with inappropriate behavior consistently.

How to use it: Fill your bottle to the brim with your favorite booze and stockpile terrible puns. Then have a buddy snap plenty of photos while you ask every girl at the party for a little snack, and go in for the kill.

3. Kissing Booth

Make it: All you really need is a cardboard box and a marker, but velvet curtains and fancy letters go a long way toward classing up this operation.

Why it works: Dude, you have a kissing booth around your face.

How to use it: Dude… you have a KISSING BOOTH around your FACE.


4. Guy in the Shower

Make it: Use PVC pipe to construct a simple scaffold. Get a translucent shower curtain with tropical fish or something equally goofy to suspend from it. Bonus points if you can track down that polka dot number from The Karate Kid. Rock some boxer briefs if you’ve got the build for it.

Why it works: You’re not only showing off your guns and your creativity, but you’ve constructed a tiny oasis of privacy that travels with you.

How to use it: Everyone sings in the shower, so challenge nearby ladies to sing-offs. And embrace your role as a welcome addition to any photo. Popular options include: Naughty Nurse Taking a Shower, Naughty Schoolgirl Taking a Shower, and, apparently, Naughty Rainbow Brite taking a shower.


Jordan Harbinger is a Wall Street lawyer turned Social Dynamics expert and coach.  He is the owner and co-founder of The Art of Charm, a dating and relationships coaching company.  If you dig this and want to learn more from Jordan and The Art of Charm team, then visit  You can also interact with Jordan on Facebook.