Halloween is my favorite time of year. My roommates and I decorate the hell out of the place, watch classic horror movies almost all month, shamble around the city as undead corpses for the Toronto Zombie Walk and, check out the various indy horror movie events around the city. So here are some tips to help you make the most of the spookiest time of the year!

Plan Ahead For Your Costume

In the past I have been very bad with planning ahead and would until the last minute for my costume, usually because I’m planning a party (see below). And there have been several Halloweens over the years where my costume just plain sucked. Learn from my mistakes and plan for this. There are literally a million ways you can go with a costume idea, so here are some ideas for PUAs:

Sexy Alpha Males – A really well done Captain Jack Sparrow is always a hit with the girls, as are superheroes, movie characters, firefighters, and policemen. Rock stars are always winners. Everyone from the Beatles to Stacee Jaxx from Rock of Ages can be damn sexy if pulled off right (photo from showcase)
Photogenic characters – there are certain costumes and characters that drunk girls will always flock to for pictures. Sometimes it’s just someone who looks EXACTLY like a celebrity or character, other times its just costumes with just the right mix of being eye-catching and being recognizably lovable by women. Really good Star Wars characters work here for some reason. My wing Wildcard looks exactly like Edward from Twilight so he rocked that look (sparkles and all) one year and was hounded by women all night. And my other wing Showcase got so many photos taken with him while dressed as Ace Ventura.
Clever costumes – What you want here is something that is peacocky, but not too ridiculous. Something that will entice girls to open you ask what you are. Be clever, but not TOO clever. If you have to explain the joke, it isn’t funny. One of my personal favorites was a guy dressed as a present, with a tag that said “To: Women, From: God”

Some tips for avoiding a BAD costume:
– Avoid going as something lame and generic like “guy with knife in his head”, the “ironically lame skeleton”, or “normal guy”.
– Avoid anything considered gross, icky, or way too politically incorrect. A blood-covered abortion doctor costume probably wont get you laid tonight (unless MAYBE you’re at a goth club).
– Try to avoid dressing as a girl, a child or baby, or something that lacks manliness or some sort of sex appeal. Wearing a dress and not shaving your chest may get you lots of photos, but nobody is going to go home with you.
– Remember that the more ridiculous you get, the more girls you will need with you. If you’re wearing a giant penis costume, you better have girls on your arm (and you should refer to them only ask your “balls and chain”). If you don’t have social proof to back up your pink hairy shaft… oh god I’m going to stop before I make a joke about being an unwanted dick in here somewhere. This is just getting obscene!
– Make sure your costume choice will be comfortable and not going to boil you alive while you’re wearing it. Remember that you’re going to have to wear this thing all night, probably in a crowded, sweaty bar or club. Lots of makeup is also a bad idea if you know you’re going to be in a place that will cause you to sweat. Also remember that if you’re planning on hooking up tonight, you better be able to a) get out of your costume easily, and b) not smell like a men’s locker room when you do.

Get A Group Together And Create A Theme

While perhaps not as much as New Years or St. Patties, Halloween, is one of those nights where nearly everyone goes out. And most people will have no idea what they are going to go as. Organize your friends and come up with a common theme that you can all wear costumes for. In recent years I’ve seen groups of Power Rangers, the Adams Family, the evil forces of C.O.B.R.A., Ninja turtles, Batman heroes and villains… hell, this year my wings and I were going to do the A-Team, but we decided on Ghostbusters instead! Roll into your favorite pub with your best mates and a swarm of girls all from the same movie, TV show, or theme, and everyone will immediately see your social value. It’s like having a whole group of people peacocking FOR YOU.

Even if you cant organize a group costume idea, take charge and come up with a plan (remember that Leader of Men attraction switch) that involves getting all or as many of them as you can together in one venue. Seriously, if you are reading this and you don’t have a plan, start looking up bars and calling people right now.

One other word of warning: if you’re doing a group costume, be cause it’s something that you can pull off if nobody is around or if everyone bails on you. Or have your costume from last year ready as a back-up just in case.

Throw A Party BEFORE Halloween

People love to dress up. Girls especially. I know girls who will spend $200 every year on a new slutty costume and then complain that they’ll never wear their old ones again. So why not give everyone a chance to rock his or her awesome costume more than once? I think Halloween is the best occasion for a party out of all the “excuses act ridiculously and drink heavily” nights. Since Halloween is on a weekday this year we get to go out on the night of Halloween wearing our costumes, but we can also throw a party on the weekend BEFORE and give everyone an excuse the show off their costume one extra night! Organize a party that weekend that takes all the things that made those children’s Halloween parties awesome, but add alcohol and adult themes. Carve some pumpkins and decorate your house – inside and out. Create a playlist of funky Halloween-related songs. Make red Jello shooters with gummy eyeballs or worms inside. Make people say Trick-or-treat before you let them in and give them candy when you do. It’s Halloween! Act like a kid again!

Pre-Party At Your Place On Halloween Night

Have people over to your place to pre-drink and get ready. Play more of those Halloween-related songs on your playlist, hang out and have some beers, and then head out together to the bar. Just don’t stay at your place too long or it might be hard to get a large group of people into the bar at once. So….

Get There Early

Make sure you plan to get to whatever venue you’re going to with enough time to avoid line-ups as well. Most of the good bars and pubs here in Toronto are going to be madhouses after 8pm and I would imagine it will be similar in other cities.

Have An After-party

Bars and clubs close, as they are inclined to do, at 2 or 3 in the morning. But Halloween, like St. Patty’s and New Years, are the nights where the single people just don’t want to go home yet. So obviously, having a place to bounce your sets to after the bar is a must. Maybe it’ll just be a bite to eat before you head back to your place, or maybe your buddy is throwing a full-blown party. Either way, have some options for the evening – or at least create some for yourself!

Don’t Be On The Prowl

Although this should just be a rule for any time you go out to a social gathering, it especially applies to nights like St. Patty’s, New Years, Halloween, etc, when everyone is out looking to hook up. If you’re the guy peacocked in the furry Cookie Monster costume, staggering around the venue – alone – while looking for girls to open, you will destroy your value and absolutely wreck the room before you even approach anybody! It will be obvious to anyone who sees you stalking around that you are just out to hook up with some drunk girl in a slutty cheerleader uniform, which makes you just like all the other AFCs out there. Instead, roll in with your friends (ideally, this should include girls!), have some drinks and share some laughs and don’t worry about scanning the room for sets to open. Women will be naturally attracted to a fun group of people who are laughing and smiling and having a good time. Create a power-base that women will give proximity to and open people nearby. Merge your sets and have someone to take lots of photos to create a massive, socially proofed vortex of spooky fun! And you will be the one who created it all. From there, the game will be easy.

Happy Halloween,