40 Conversation Starters for Any Voyage, Short or Long.

I love sailing with people that I have just met, and, of course, I want them to have a great experience and I, selfishly, also want to have a great experience.

Sometimes there are lulls in the conversation, and if you want to get a nice small group to chat, here are (I think) some great questions to ask… starting with the one I ask almost everyone who boards a boat with me:
What is your favorite boat name, and why? (for clarity, this is not necessarily the name of a boat you own) Boat names seem to have some important meaning to their owners and almost always have a nautical theme, so I ask my passengers to come up with the name that they want to bestow on a boat… it tells me something about their personality. I also always give them one boat name I really like. For example, I spent many years as a real estate agent, and when I set out with 2 of my real estate agent friends to buy a boat, we discussed calling it Reeltor (Realtor, but like a fishing reel)

Here are a few others:

• Tell me about your best day on the water.
• If you could have a superhero or cartoon caracter for a best friend, who would it be?
• If you could have any real animal as a pet (so not a unicorn or bigfoot), which would you choose and why?
• Where is one place you’d love to travel to again?
• What’s your favorite comfort food?
• What was the best meal you ever enjoyed?
• What do you love most about your home?
• What gives you goosebumps?
• Tell me about your childhood best friend.

• What’s one habit you want to improve on, one habit you want to get rid of, and one habit you want to keep “as-is”?
• If you were to sing a duet with a famous singer, living or dead, who would it be and why?
• Who do you most admire, living or dead?
• What was the first big ticket item you pruchased as an adult?
• Have you kept any meaningful memorabilia from when you were a kid?
• What instrument that you don’t play, do you most wish you did?
• If you could travel back in time, specifically to your life, when would you go back to and why?
• What is the compliment you hear most often?
• What’s your earliest memory?
• What are some of your best memories about your parents or whoever raised you?
• What is something you have accomplished so far that your younger self would be very proud of?
• What did you like most about school? (and don’t say nothing… even if you did not like school much, there was something you liked)
• What superpower do you wish you had?

• What superpower do you have? (your best real trait, like negotiating or ??)
• What accomplishments are you most proud of?
• What is the best thing about your house?
• What do you want to be when you grow up?
• If you could live in any other country for 1 year (money is no object), where would you go?
• What’s one of your favorite memories from your childhood?
• What was your favorite subject in school? Which characteristics are you happy that you inherited from your parents?
• What food reminds you most of home?
• What about the state of our current planet would be most surprising to your younger self?
• What was your very first job?
• What’s one act of kindness you experienced today?
• What do you do for enjoyment?
• Do you prefer being around other people or spending time alone?
• If you had a whole day to yourself, what would it look like, what would you do, and where would you go?
• Who do people tell you you look like?
• Do you collect anything?
• What’s one thing your loved ones would be surprised to learn about you?

If that does not spark some interesting conversations, please find people who are alive LOL.

Fair Winds
Captain Jeff Vegas