Traveling Alone: The Crazy Stranger Challenge

Monkey Me
Making friends is easy!

Traveling alone is awesome.

Traveling alone sucks.

I plan on writing a more detailed overview of my experiences as a solo traveler when I finish my trip, but for now I wanted to share a quick thought that I had today and then to ask you all for some help.

Feel free to read the background thoughts or just skip to the bottom for the challenge.

Approach Anxiety

We’ve all been in situation where, for whatever reason, we want to talk to a stranger. They could be some attractive member of the opposite sex, a celebrity you see on the street, or just someone who you find interesting for whatever reason.

We want to go over and talk to them, but it’s difficult.

The degree to which this is the case varies based on the person- e.g. introverts might have a harder time with it than extroverts (although that’s a totally different can of worms that I won’t get into right now- shyness and introversion have been shown to be fairly disparate), but almost everyone has this feeling to some extent.

But what is this feeling exactly? Why is the simple act of talking to someone difficult? Isn’t it something we do every day?

I would posit that this anxiety is really just the fear of being judged. We want to go over and talk to them, but what will they think of us? Will they think it’s strange? Will they think I’M strange?

There are three main workarounds that I have found for this problem.

  1. The hard way: change yourself. Keep telling yourself (perhaps in the 3rd person) that the world won’t end if you go and talk to someone, and maybe you’ll start to believe it. Or at least you will after enough practice. I’ve been working on this for years but still have a ways to go.
  2. The easy way #1: do something to artificially ensure that they won’t think you strange.
  3. The easy way #2: do something to yourself to artificially ensure that you won’t care if/when they do.

The latter two are the ones that I want to focus on right now.

The second can be accomplished by putting yourself in situations where starting a conversation would seem totally normal. This is how something like speed-dating works: they are able to mostly eliminate approach anxiety by imposing a setting where you are required to talk to someone, so at least the act of you starting a conversation won’t be judged (what you say is of course a different matter).

One way that I have found this method be applicable while traveling is in the difference between meeting someone during the day vs at night.

If I happen to be staying one bed over from someone at a hostel or sitting next to them on a bus, it’s quite natural to start up a conversation. Hostels tend to be very friendly environments where everyone is open to meeting people. If I have to sit next to someone for an extended ride then saying a few initial words is just polite.

Now fast-forward a few hours. I’m now at a bar by myself. Like a creeper™. Suddenly that same girl who would have been totally friendly when chatting back at the hostel will think I’m weird if I just come over and just start talking to her at her table (or at least my instinct is to assume that to be the case).

Thankfully I’ve so far been able to avoid the above situation by just making friends during the day or arranging to meet people at night, but not every day can be a winner.

This brings me to Method #3.

The easiest example of this method the Costume Phenomena. Put yourself into a crazy enough outfit and suddenly it’s not you that they’re judging anymore.

Everyone wants to talk to a gorilla:


Even for less full-coverage costumes where your face is visible, you can still effectively hide behind the alternate persona.

But while this method is loads of fun, it’s hard to really apply in too many different situations.

Instead, a lesser version of this method involves changing not other people’s perspective of you, but your own perspective of the interaction. When someone dares you to go and high-five a stranger, you may feel a bit nervous, but it’s not too bad because at least YOU know why you’re approaching them. It’s someone else’s fault. Any judgement should really apply to them.

This finally leads me to the real point of this post.

The Stranger Challenge

I’ve started to play little games with myself both to give me an added kick to go meet people and just to make the interactions more hilarious.

Last week I played the accent game for a few days. One night I successfully convinced two Irish girls that I grew up in Dublin, but they were able to guess that something was off and that really I also had one parent who was British. The next day I kept it up and thoroughly confused a newlywed couple at Chabbad visiting from Canada.

I have plenty more ideas for things to do that are successively more crazy, but I think it would be way more fun if the challenges were actually externally imposed. I am therefore throwing down the gauntlet to all of you: post a comment(s) with some type of challenge for me to do involving strangers, and up/downvote other peoples’ suggestions. I’ll see how many of them I can manage to do over the next week.

Let the craziness commence!