How to Win at Halloween

Tom Cruise, Little Red Riding Hood and a boxer walk into a bar. Cue hilarity.

No, this isn’t a scene from a movie, but rather a fun-filled Halloween night complete with pizza, freaks and jello shots.

Past Halloweens have always been fun, but none of them compare to a Halloween in New York City. Not only are the freaks out in full force, but the fun is escalated and there are literally no worries, absolutely none. You don’t even have to worry about someone being a sober driver!  There are a few guidelines, however to make sure you have a great time. By taking you through my fun, candy-filled, glorious day, I am going to outline a few of my new Halloween guidelines. The only thing that was missing from my day was binge-watching Harry Potter, but that’s what DVDs are for.

1. Spend all day getting ready with your friends.

Okay, no one is more fun to get ready with than your best friends, because no one wants to get ready with the person they are dating… that is just weird and uncomfortable. Meet them out, but get ready with your friends. You can drink, amp up the ridiculousness and eat as much candy as you want (because that IS the main point of Halloween). Also, this is the perfect opportunity to try out your accents, make up, dance moves and whatever else you plan on doing that night.


First of all, plans are for losers and they will probably get ruined anyway. Instead, what you SHOULD do is make an outline, maybe hit a few of the things you were intending to do and just wing it. Halloween, especially in NYC, is a go with the flow deal. As in you need to go with the easiest flow of traffic and avoid all the freaks on 6th Ave.


If you enjoy standing in the middle of a mob, surrounded and smushed between strangers wearing masks and costumes that may or may not have real blood on them, then the Halloween Parade is definitely for you. If, like me, you can think of a more pleasant way to kill an hour or two, then learn from my mistakes and just avoid the parade all together.

Some better alternatives are drinking, eating pizza and drinking some more. Keep in mind, this is BEFORE you go to bars. Also, Halloween is a marathon, not a sprint. Learn from my mistake, again, and eat something other than candy.

3. Make your own costume

I spent all day (0kay, one hour) sewing my Red Riding Hood costume, and it gave me the right to be obnoxious and brag about it for the entire evening. Other people may disagree with me (here’s looking at you Tom Cruise), but when you prick yourself with a needle one hundred thousand times, then you have earned the right to say, “Hey, like my cape? Yea. I MADE IT.

Also, my costume cost me $4. So I am the real winner in this scenario.

4. Commit to character.

If someone asks you where you live, you DO NOT tell them the truth. No. You are in costume, friends. You must always stay in character.

12065868_10153917562592985_1940054964091579815_nFor example, last night I had this lovely conversation with a stranger. In a circle with Tom and Rhonda (the boxer), a whoopee cushion asks, “So where do you guys live in Manhattan?” Rhonda says, “Well Tom lives in Chelsea and I live in Long Island City.”

Then I jump in, “I live in the woods.”

END. SCENE. Do it. It’s fun.

5. Make sure your team is playing in the World Series.

Again, this will give you talking points for the entire evening. Also, it will give you an excuse to yell at, argue with and trash-talk anyone who disagrees with you. Also, celebratory shots are completely acceptable. In fact, they are encouraged, even if no one takes them with you or knows that you’re taking them.

6. Act ridiculous.

Halloween is one of the few nights you can act like the total crazy freak show you always struggle to suppress (don’t deny the truth in this). Acting like a ridiculous hot mess is a great release from all of that pent up frustration from the boring desk jobs we all love to hate. So, this means ditching Hitch’s rule and dance like a loser. Drink a little more, talk a little more, and laugh like your life depends on it. You will only benefit from this. And hey, if you’re like me this will soon become a staple in your everyday life. Don’t suppress your crazy side, EMBRACE IT. It’s there for a reason.

7. Meet new people.

And maybe kiss them if you get the chance. Again, it’s Halloween you cannot lose. Chances are you don’t even know what they really look like, so you won’t be able to have “post-bar kiss regrets”. And, if you’re lucky, you will put your number in their phone with some ridiculously long name that will only bring more joy and laughter into your life such as, “Alex Red Riding Hood Royals Are Asesome. World Series Champs.” Notice the reference to No. 5. My only disappointment was the fact that I had a typo in there because I struggled for a good 10 minutes to not have one (I didn’t want to seem like I was that drunk).

But, be nice to them. This is a, “do as I say and not as I do” moment. If someone tells you they are an eagle, you might think it’s funny to call them a duck all night and look up pictures of ducks on Google to prove your point, but….. okay no that was actually really funny. If you are mean, but funny about it, I guess it’s okay. Just don’t be too mean, especially to strangers.

New people are fun, and your interactions with them might even lead to a great story to share the next morning. BE CAREFUL, however, because you don’t want to make too many poor life choices…. There’s always a line, draw your own when you are sober and STICK TO IT.

8. Go HOME with your best friends.

Here is my one moment of maturity and wisdom, because Halloween DOES bring out a lot of freaks with bad intentions. Just like my last line above, it is always important to draw your own line when you are sober and stick to it, but going home with your friends on Halloween is very important, because how do you REALLY know whom you just met under that mask? You might not even like the way their face looks! And, do you really want a stranger to see your costume makeup smeared all across your hungover face the next morning? I think not. Do your hungover self a favor, and just go home with people you know still have to love you in the morning.

9. Order bagels the morning after.

By the next morning you are probably a hungover, reminiscent, hot mess. Why deny yourself one of God’s gifts to earth? Order NYC bagels (if you don’t live in NYC that sucks), and stuff your face with the pure goodness of carbs. There is absolutely no reason for you not to. Halloween is over. You don’t have to worry about showing that much skin again until June, so live it up. Time to put on that holiday weight! Okay, that was a joke.. kind of… maybe…

10. Reminisce all day with your friends.

Or, if you are me, also type it all out for the whole world to read… They are called memories for a reason. You want to REMEMBER them (I just made that up, but it sounds pretty accurate). You will laugh at yourself and at your friends. You will probably want to curl up into a ball at some point in embarrassment. But, if you did Halloween right, you will spend all day wishing you could go back and re-live the epic adventure. Which, if you’re me, will probably be next weekend.

Just because Halloween is over, that doesn’t mean you have to stop being a little ball of ridiculous fun. Take Halloween with you wherever you go. Where your hand-made red cape to a bar sometime, I am SURE you will get lots of compliments (fair warning: I actually plan on doing this).


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