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Through talking to many shy and socially insecure people, there’s a cruel irony I’ve discovered.

Many crave the ability to talk to the “cool” people in places like bars, clubs or on the street. But unfortunately, talking to those people in those places feels impossible.

“Popular people” are generally more “picky” and dismissive in those types of “cold” social settings. And the fact rejection seems more likely to you makes these the hardest places to engage strangers if you aren’t already confident and skilled socially.

Well, if you’ve read any of my articles before, you know I advocate practicing your conversation skills repeatedly. This grows your skills AND confidence so you gradually expand your comfort zone.

But how can you practice in places like bars when it’s so hard to even start talking to people there?

Well, what if it could be easy, even for just one night out of the year? What if there was a way for even insecure people to easily start conversations in these intimidating yet alluring places?

Make Conversation Practice Easy by Going Out on Halloween

In my experience, Halloween is one of the best nights of the year for a socially insecure person to socialize in a bar. Yes I’ll admit, saying it’s 13 times easier is just in the spirit of the season. But I DO know from experience starting conversation is exponentially easier on Halloween.

Because on Halloween, talking to people you don’t know in places like bars and clubs is expected. In other words, you have the perfect conversation starter built into the event.

“Aw, that costume is awesome!” OR “Whoa…ok. I give up. What IS your costume?”

Some variation on the above two lines is the conversation starter everyone engages in all night long. Not only is it expected, people WANT you to comment on their costume.

It also works great when you recognize what someone’s costume is and compliment them on it. This works even better if they’re an obscure character, like say Starswirl the Bearded ;)

That’s High-5 worthy right there!

Why Halloween Makes Starting Conversations Easier

Basically, Halloween makes the normal “cold” social setting of bars and clubs more “warm.” It gives everyone there something in common to talk about. Plus, because of the nature of the holiday, most people are in a playful, positive, and open mood.

This makes the starting a conversation part of things less anxiety provoking.

After you make a comment on their costume, continuing the conversation is also easier.

Maybe you talk about fond memories you have related to their costume/character

Maybe you ask why they chose the costume, then talk about your costume a bit

Maybe you discuss other costumes you’ve each seen people wearing that night

Throughout all of this chatting, it’s likely free information about them will come out. You can use this to continue the conversation in a different direction. Just remember, the above examples are only to show you that simple topics CAN work.

But my advice is to stray away from rehearsing what you will say or creating pre-planned material.

Remember, you’re working at moving through a conversation in the moment, NOT at performing a script you planned in advance. In most cases, pre-planning what you’re going to say only makes you MORE nervous and you end up sounding awkward.

3 Tips to Talk to MORE People with LESS Anxiety This Halloween

1. Practice at YOUR Skill Level

If you try to push too far past your current comfort zone, you’ll make yourself overly anxious. All that does is cause you to freeze up and not talk to new people. Instead, take baby steps. That’s the key to stop being shy.

So if you normally have trouble starting conversations with strangers, make JUST THAT your goal. Start say, 5 conversations during the night. Just comment on people’s costumes in a positive manner and get their response. That’s it. If you’ve done that, consider the night a success.

On the other hand, if starting a conversation like this isn’t that big a deal for you, aim a bit highter. See if you can keep the conversation going for a few minutes after you start.

The point is to push yourself out of your comfort zone, but not too far. That way you’ll still see success without feeling overwhelmed.

2. Wear an Awesome Costume

The benefit of wearing a good costume is others will stop YOU to talk about it. This gives you more “stranger practice” without having to approach as many people.

Now you can either buy a good costume OR put time and effort into making a clever one. The second is my favorite way to go. You don’t have to spend a lot of money on it either. You can often use stuff you have laying around the house.

For example, one of my recent Halloween costumes was a “Teenage Mutant Ninja Turtle Nose.” Since it was funny and clever, I had people coming up to me all night asking about it.

So if you’re extra creative, make your costume unique or even obscure. For those who “get it,” you’ll create a strong connection. For those who don’t, they’re more likely to stop you and ask because they want to know what the hell you are.

3. Wear a Mask

Philip Zimbardo, a famous shyness researcher, describes how his younger brother overcame shyness with a paper bag. By wearing the bag over his head to elementary school, the boy gradually became more and more outgoing. The anonymity of the paper bag made him bold enough to act in ways he normally wouldn’t. Eventually he was able to be outgoing without hiding behind the bag.

You can use the same concept on Halloween with a mask. It can be a small Zorro type mask or a full face mask. Go to the Halloween store and test which makes you feel more liberated.

The point is, spending Halloween behind a mask is an opportunity to jump past your normal limitations. Even if it only helps you be bold and confident for one night, you’ll see what it feels like. You’ll see what’s possible.

Have an Intention to Practice, NOT to “Be Liked”

The most important tip to remember is this: The night IS NOT about trying to get people to like you or making friends. If those things happen then fine. That’s just icing on the cake. But again, it’s not what you’re trying to achieve. Because having that mindset will make you more anxious and needy.

No, your goal is just to practice being more social by commenting on costumes and perhaps seeing how long you can keep the interaction going. That’s it, that’s all.

Don’t get me wrong…your anxiety will still be there. But the barriers to connecting in the bar setting will be much lower than normal. It’s just too good a practice opportunity to miss.

And remember, if you’d like more tips on how to do well socially, sign up for my free Conversation Tips Newsletter. In it, you’ll get exclusive tips on how to be more outgoing and confident as well as blog updates and news on my upcoming Friendship Blueprint E-book.

(Photos courtesy of Rob Boudon & JD Harvill)