The 5 Stages of Roadtripping with a Stranger

Like the 5 Stages of Grief, but way better.

“Stranger” may be a bit of a stretch, since Kass and I were basically friends in the making. But it is true that we barely knew each other when Kass asked me to hang out the following weekend. Somehow, “hang out” turned into spontaneous-four-hour-road-trip-to-San-Francisco. Naturally, being the crazy travel advocate that I am, I was all in. Which leads us to…

Stage 1: The “Yes” Moment

This is a brash attempt to get a movie made about me called “Yes Woman.”

As propagated by Jim Carrey’s excited face in this picture, “one word can change everything.” If you do not say yes, I guarantee that you will not go on a road trip with a stranger. And that’s my 100% Yes Guarantee (patent pending).

There are a few reasons why you should say yes to a road trip with a stranger:

  • While you say “no thanks” or “next weekend” or “next year”, life passes you by. The world keeps spinning. The only perfect time is now.
  • It is your sole responsibility, and no one else’s, to make your life an adventure. Take accountability for your own happiness.
  • In the words of Bill Nye“everyone you will ever meet knows something you don’t”. You already know everything there is to possibly know about yourself. If you’re nervous about talking to someone you don’t know, focus the conversation on the other person. Not only is it more interesting than talking about yourself, but it makes conversation all the easier for you. Someone who you don’t know well is like a Pandora’s box of exciting learning material.

Important: Trust your gut when choosing the stranger. While I say “stranger” for the sake of this article, I really mean an acquaintance, or someone who is a safe person to be around. Please, do not find some random dude on the side of the road and drive him to San Francisco. Be smart. And let your loved ones know where you’re going, who you’re going with, and when you intend to be home.

Stage 2: Brief Anxiety

Let’s face it, I’m not as utterly chill as I appear to be. I am the exact opposite of chill. To be honest, I was a little nervous about going out into The Great Unknown (San Francisco) with someone who I didn’t know that well.

To be successful on a road trip with a stranger, find your “go with the flow” mindset. If you are still super nervous, set expectations before you set out on the road. Explain your eating habits, how you expect payment for gas/food to go down, any health or allergy restrictions you have, and any other pressing issues. Focus on coming to a mutual agreement on what’s important to each of you. Setting expectations will alleviate any anxiety you might be feeling and help you enjoy the journey.

Stage 3: Commit

Commitment happens before, during, and after a road trip. The Cardinal Rule: Do What You Say You Will Do (DWYSYWD). 

Before: You’ve just said yes. Now it’s time to commit. Finish your work ahead of time, pack your bags now– not the night before, and make arrangements for child/pet care. No. Excuses. Do not back out! You are going on an adventure. Make your preparations as soon possible after you say yes. DWYSYWD.

During: It’s even more imperative not to flake out during the roadtrip. Don’t be the guy who fails to chip in for gas, ditches your newfound friend, or shows up late when it’s time to embark. Heck, don’t be the guy who jumps out of a vehicle at 65 mph. You said yes, you set expectations, and now you’re committing to being a great road trip buddy. Be the road trip buddy you want to see in the world.

After: After your road trip, settle any bills that may have incurred. If you promised you would pay someone back for dinner on Saturday night, DWYSYWD and pay them back. SAY THANK YOU for any hospitality you received, whether someone let you crash at their pad, fed you a delicious meal, or gave you great advice on what to do. Lastly, and most importantly, show your gratitude to anyone who may have done a favor for you while you were away. Whether someone walked your dog or watered your Venus flytrap, they went out of their way for you. Say thank you.

Stage 4: Get to Know Your Neighbor

I usually say “Get to Know Your Neighbor” out of sarcasm during a very claustrophobic situation. For example, when I’m smashed like a sad sardine on a bus full of people, I find this phrase very fitting. Anyway, during your road trip, make it a point to get to know your road trip buddy. You’ll be spending lots of time together. This is a great opportunity to turn your stranger into a great friend.

Two Strangers on a BoatWhile getting to know your neighbor, seek activities during the trip that you wouldn’t normally do. As an example, it’s not that I don’t like boats, but I’ve never had an overwhelming urge to get on a boat. During our road trip, Kass and I went on an awesome boat trip with some friends in San Francisco. Boating ended up being one of the highlights of our entire trip! You’re already on a roll with saying yes. Keep an open mind and continue saying yes to adventures outside of your comfort zone (but ideally inside your price range). A fun idea would be each choosing one activity that is outside of your comfort zone, and then doing each activity together.

Stage 5: Entering Your Millionth Hour Together

It’s no secret that you will spend A LOT of time together on a road trip. This is one of the coolest parts about traveling with someone you don’t know well. If you want to take the connection deeper, I recommend The 36 Questions That Lead to Love.

The 36 Questions create a meaningful conversation with anyone, whether it’s someone you’re dating, a stranger, your mom, or old friends. Last year, my three best friends and I did the 36 Questions during a road trip. I learned things I never knew before about the three people who I considered myself closest to. It was one of the most special and memorable conversations I’ve ever had.

Even if you don’t do the 36 Questions, use your time together for some out-loud reflection on life. You’ve taken a huge pause from your normal routine. Did you learn anything you want to apply to your life when you get home? Reflect together to find meaning and connect.

The End?

Before you even know it, your roadtrip will be over. You said yes, overcame nerves, committed, got to know a stranger, then dove deeper into that connection. Up next: another yes moment!

Your Voice

Did you experience the 5 Stages during your last roadtrip? The comments are yours.

A huge Thank You to my new friend Kass for encouraging me to get out of my box last weekend. I’m glad you’re not a stranger anymore. *insert awkward wink here*


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