How to Start a Conversation

Let’s explore how to start a conversation. Having an authentic conversation all begins with showing people you care about their souls.

I used to own a bed & breakfast. I had such a fun time teasing and chatting it up with guests. I learned a lot about people, talking, and laughter.

A few of years ago, I wrote a blog post for my famous mud pie recipe and added some fun with the help of the book “How to Win Friends and Influence People.” It remains one of my favorite footprints I have placed out on the interwebs. (Be sure to check it out.) Although that post was all written in fun, there are some great ways to start authentic conversations that we can all apply.


A smile may only stretch across your face but people feel your joy for miles when you use it. A smile begins the conversation before one word is even said out loud. It states that you are open to conversation.


Don’t be afraid to tell someone when he or she gives great service or that you really like their tie, earrings, or whatever. Be honest and they will feel special.

Be a Little Silly

When I owned a bed & breakfast, one couple told me of all their B&B experiences when we first met. They mentioned one inn had delivered McDonald’s breakfasts to the breakfast table. I couldn’t help myself. No, really. I simply couldn’t. I had to serve McDonald’s for breakfast as well. The gentleman turned white until his wife burst out laughing. I then gave them their real breakfast. Best. Morning. Ever. We’re still friends, the McRaes and I – yes, that’s their real name.


Sometimes we meet people while they are going through a really significant loss. Show you are sorry for their loss. Try to put yourself in their shoes in your mind. Don’t compare their story to yours out loud; but, instead, relate inside the best you can and focus on their story. Be a good listener. Sometimes the best way to show you care is to just listen.

Ask Where They Grew Up

Some people think they’re too shy to start small chat but it’s not hard to do when you commit these conversation starters to memory.

Where did you grow up?

What was your first car?

What are you up to this weekend?

What kind of dog is that? How old is he/she?

Have you been here before?

Are you on twitter too? Here’s my card. I’d love to stay connected.

Make your own list that caters to the crowd around you. Create your own questions that relate to whomever you’re chatting with so you’re prepared. Use your questions often so it becomes easier & easier to make friends. Remember, these can feel artificial if the questions come at them thoughtlessly, so be sure to be present and really listen. Use these questions for starters and then let the conversation flow naturally. Machine-gunned questions freak people out. Don’t be afraid of pauses – they are natural too.

Don’t Keep Inside Jokes Inside Yourself

If something hilarious happens in front of you and someone else, use it to giggle together and then introduce yourself. Ask them if they live in the area. Acknowledge that you just shared something funny. If it happens in front of the grocery store clerk whom you see weekly, bring it up again the next time you go to the store. People love being remembered and sharing memories with others.

There’s a small part of me that was filled with joy when I checked guests into the inn one day and the neighbor’s goats decided to come for a visit inside the B&B. The guests and I became goat herders. I’m pretty sure they’ll never forget that day and neither will I.

Make The Most Of The Moments That Mortify

Finally, one of the biggest fears we have when it comes to opening up socially is that we will fumble around. Fumbling is okay. As Seahawk Russell Wilson said once, “My career will not be defined by one play.”

The worst that can happen is you will end up with a hilarious happening which allows for a conversation in and of itself. People love reassurance you are human too.

Try these tips and let us know what happens! We love hearing your stories.

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