Travel Tip – Tips For Creating Fun Conversation Starters 

Travel Tip

for creating fun conversation starters

Hello everyone,

In keeping with the theme that I started last week, on tips and tricks that will help you with social anxiety and how to start a conversation. These tips work anywhere anytime not just when traveling.

This week’s blog is for those people that still need a little help. I bring to you another awesome tip for starting conversations. Some of these will no doubt take you beyond your comfort zone but remember, all the best stuff is on the other side of that comfort zone.

I recently saw a post in a Facebook group for travel, from a young woman in a swimming pool looking a little sad and lonely that went something like,

“that moment that you hear a group of people having a great time and you realize that you are all alone.”

I travel by myself often and I’ve gotten good at striking up conversations with random people but sometimes you need a little help to get started or you just might want to bring the fun along with you. There are opportunities to have certain things with you that spontaneously creates conversation. These tips work whether you are alone or in a group. Here are a couple of scenarios I have run across over the years.

Use props that stimulate curiosity

Use props that have significance to you, or your traveling group, to generate conversation. The wilder or most outrageous, the better. One time, I saw a group of about 12 people, both men and women going through the security check all wearing purple. They wore purple wigs, hats, purple beads, glasses and teeshirts. They immediately attracted curiosity, which in turn stimulated conversation. Everyone in that TSA line wanted to know what was up with the group. As it turned out, they were going to help support a friend that had cancer and purple was her favorite color. Not only did it act as a catalyst for conversation, but it also brought awareness to cancer and I feel acted as a reminder of how lucky we all were and then the capacity of love. I’m pretty sure the whole TSA line were saying a secret prayer for their friend with so many people wishing her a positive outcome and wellness. I believe all that good energy probably found it’s way to her and helped her out. I have thought about that woman and wondered how great a person she must have been to have a group of friends like this to surround, love and support her.

Step Outside of your Comfort Zone

I have long considered myself to be a woman with a comfort zone that stretches pretty far compared to most other people I am always amazed when I find another person that does stuff that makes me pause. I have a friend that often does just that. I bow down to my friend Patricia from New Jersey. Not only is she waaayyy more well travelled than I am, (I am super jealous) but she does it with a flair unlike anything I have ever seen from anyone else. Her Flair? Something she refers to as the Happy Hat. She makes large brimmed hats from papermache using newspaper and then puts on a plethora of stuff including but not limited to streamers, toole, fabrics, small teddy bears, replicas of birds in a nest, lights, bows, ribbons, you name it. The bigger, the bolder, the brighter, the better. She brings these happy hats with her wherever she goes and she almost always has a spare one for her friends to join in the fun. Here is me in the line at Notre Dame in Paris France wearing a Patricia original, Happy Hat.

I always refer to it as the magic hat, Why? Because it’s just plain magical how it attracts people to you and makes them wonder and then ask,

“What’s up with the hat?”

It stimulates curiosity. We had many fun conversations while waiting in line to get into Notre Dame. By the way, that is me and another friend of Patricia’s, not Patricia herself. She loves to spread the fun of the Happy Hat.

Yes, we respectfully took them off when we went into the church.


Additional prop ideas

Although I did not personally witness this, I did get this story from a reliable source. A long lost cousin of mine attended a family reunion, (on purpose) she wore one black shoe and one red shoe (make sure the heel length is the same so you don’t get hurt) of course this generated conversation for people to say “Your shoes don’t match.” and that would be her lead in to say, “Yeah, I know. I did that on purpose, I wanted to meet you today…” Starts conversation.

Cautionary Props, some things work and others don’t

One time, not long after 911, I was working on a data center migration from the US to the UK and we decided to try using commercial airlines to transport data tapes during a dress rehearsal to see how it went. I had two big, black cases with big signs that said cannot be put through an X-ray machine or any magnetized scanner. Although I kind of felt like an international woman of intrigue and mystery. I could tell the general population in that TSA line were very uncomfortable with it. I got a ton of dirty looks and clearly people were nervous. The one brave soul asked me what was in the cases, and I said, trying to be funny, that I couldn’t tell him otherwise I’d have to kill him. Needless to say, he did not laugh. I was feeling kind of cool right up until I got to the entrance of the plane, where I was knocked off my high horse and curtly informed that the airline personnel would NOT help me with my baggage. The cases were like 50 pounds apiece. I had to schlep the cases to the appointed seats by myself. Luckily my seats were relatively close to the front of the plane. It was hard, but I got it done. After they showed up with some crazy belt extenders for the cases we were on our way. Beside the fact that I love to tell this story there is a point here. Don’t try to make yourself look like an international man or woman of mystery, it will only result in more isolation.

Alternative prop options

Now you may say, “Margaret, that’s all well and good for you and your whacky friends, no offense, but I am NOT going to wear anything like that Magic hat or a purple wig. I would never do that.” (With the emphasis on the word Never) (My publisher hates it when I do that, evidently making it italicized is enough, but screw it, I’m throwing caution to the wind.)

If you are not one of those intrepid brave souls that would like to stimulate conversation by wearing a whacky wig or hat or mix matched shoes or super flashy socks, then try one of these more subtle conversational props.

I have seen an older gentleman using/carrying probably one of the coolest walking sticks I’ve ever seen. It was beautiful, a work of art. That created conversation. You need to find something very unique to set yourself apart. I was in an airline boarding line with a young couple in front of me and they had a daypack with a really cool hand embroidered piece of cloth that had a cool saying on it that was sewn onto the backpack for everyone to see. It was kind of like a bumper sticker for when you are waiting in the TSA line or the boarding line, it’s kind of in your face and but more importantly, it stimulated conversation.

Check out my little video that gives you a great, easy and inexpensive idea to use a prop that not only helps to stimulate conversation but could save a whole plane of people as well. I hope you enjoy!




Here is an additional link to help you start up conversations:

Although props are not a technique in this article, it is a good article to help you start conversations in a fun and interesting way . The article is titled “15 conversation starters that don’t suck!” Enjoy


In Conclusion

Look to stretch your comfort zone a little and wear something outrageous that will have people smiling and will generate curiosity. That in turn will stimulate conversation.

Look to use props to bring in your own personality, only amplified. Something that you love, that will have you enthusiastically talking with another person you don’t even know!

After establishing the connection, ask the questions of the person you were just talking to “So what about you? Where are you headed?…”

Smile – it makes the other person feel like you are open and approachable.




Lessons from the Road USA

Lessons from the Road, USA shares the travel adventures of a funny, single, 50-something year-old woman, traveling across the U.S. in a pickup truck. Webster is navigationally challenged and yet strangely addicted to camping sites and critters. She visits monuments of historical or personal significance and meets some fascinating people along the way!

Coming Soon!

Lessons from the Road RV

Join Margaret as she shifts from her tent to a new RV. This book is a must-read for anyone who owns, or is thinking of owning an RV to travel full-time.

Podcasts Featuring Margaret

Get Focused Episode 80

Episode 80: Meet Margaret Webster, author of “Lessons from the Road: USA”

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