Cruise Ship Conversations: Turning Strangers Into Real People

Transatlantic Crossing, April 2025

Because my cruise was a one-way “repositioning” cruise and school was still in session, the demo skewed to older retired couples. I was surprised at the number of folks who were in the midst of a three-month (or longer) journey where this cruise was just one piece of multiple connecting cruise itineraries. I think a lot of them had similar objectives to mine – enjoy the ship while you simply live your life. I was there to focus on writing projects. Not having to worry about cooking or cleaning or driving anywhere made it a lot easier.

With my own agenda, I didn’t socialize much. I wasn’t interested in evening shows, the casino, or group gatherings. The ship had a get-together for solo travelers, but I thought making friends would just slow down my work. I kept to myself. It was kind of entertaining to sit in the pool area or the dining area of the Lido Deck and eavesdrop and observe while I ate lunch. But to my shame, I found myself stereotyping and shuffling people into a “boring retired person” category far too often. All it took was an unflattering polyester shirt, maybe a slower walk, or an overbearing conversation with a server.

I didn’t realize how much I was doing it until I talked with Rich and Sara. They were seated across from each other by the window and I was at the end of the table, a chair separating us, during lunch. I was only vaguely aware of their conversation and of Sara telling the server she needed coffee with her dessert to “offset the sweetness.” When I got my own dessert, Rich looked over at it and I said, “I usually tell myself it looks better than it tastes.” And I agreed with Sara that I like to have coffee with dessert. That set off a conversation that miraculously turned them into Real People.

When Rich retired from the Navy, he worked for Lockheed Martin as a system engineer. I talked about how my sons turned their military experience into solid careers. He’s been fully retired for 10 years and they were now in the middle of a trip that would take them to Morocco, Amsterdam, and parts of England. Sara was the consummate Navy wife, adapting to new locations as needed, from San Diego on the west coast to Norfolk on the east. We talked about the challenges and benefits of buying and selling houses. Sara felt lucky that on one base they had a gorgeous view of the water, even though they didn’t have a lot of status and money. They met in college in Ohio, have been married for 50 years, and have three children. When I asked to take their photo, they didn’t hesitate, and when I got up from the table I felt like I’d met new friends, even if I never saw them again. They were interesting, fun, and definitely not boring retired people.

I started chatting with Kim and Michael, a couple from Nashville, while we were waiting for the ferry in Bermuda. We’d been walking around the capital city of Hamilton and were ready to head back to the wharf where the ship was docked. Michael was retired, but works part time at the Grand Ole Opry. He says it’s a lot of fun, and even set up his son with one of his coworkers. That coworker is now his daughter-in-law. I got Kim’s number to share the photo I took with them, and Michael suggested we get together for dinner while we were on the ship.

Of course, conversations are unavoidable in the formal dining room. When I wanted conversation, I dressed up and went to the dining room where they would seat me at a table for six. The first night, I was seated next to one man who I thought was really out of it. His wife took charge of their orders and seemed slightly rude. My impression of the man totally changed when he turned to me and started chatting. He is deaf in one ear, has a cochlear implant in the other, and is losing his peripheral vision. He told me those dinner settings were really challenging for him. He turned out to be a real sweetheart.

Then there was Doug. He is retired, but during the course of the conversation he talked about being a private pilot. We talked about some of the recent air mishaps, including a helicopter that had just gone down in in the Hudson. He knew what he was talking about since he’d served on a review board that examined aviation accidents. But it wasn’t until the very end of the dinner that I learned he’d worked as a body guard before his aviation career. He started telling stories of close calls and high risk. I looked at the woman beside him and said, “Were you married then?” They looked at each other and both said, “Oh we’re not married!” But she pitched in on how traveling with him was interesting because he was always on high alert. They‘d been traveling in a foreign city together when he leaned over and whispered to her that they were being tracked. He pointed out a woman ahead of them and a man behind them who were about to try to engage them. Doug turned abruptly, walked back to the man, got in his face, and both the woman and man took off. During his career, Doug had a broken nose, broken ribs, and various other injuries. He said sitting in the dining room with us made him nervous because his back was to the entrance, but he used the mirrored columns to track the comings and goings of the servers.

It doesn’t take a full dinner conversation – just a few minutes, really – to change a stranger into a Real Person. Once they become Real, it’s harder to be dismissive or unconcerned. I wish people, including me, made the effort more often.

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Tips & Recommendations for Starting Conversations

  • Most of my conversations are sparked by the smallest comment. It can be about anything: something you are both seeing, how you feel, something that surprises you.  Some people like to ask where you’re from. If someone wants to engage, it’s easy to start the conversation with something simple. If they don’t, no harm done and just move on.

  • Look for ways to help. When I went to buy a ferry ticket in Bermuda, the British couple in front of me were upset to find out the visitor’s center was cashless. They hadn’t brought their credit card with them. I offered to put their tickets on my credit card and they could pay me with their cash. They were very grateful, and it set off a nice conversation about their trip.

  • Of course, be sensitive to social clues. Are you talking more than listening? Does the other person seem to be interested? Is their body language saying they’d rather be somewhere else? Keep it short and interesting, and find something else to do when the conversation is done.

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I Probably Shouldn’t Be So Annoyed by Cruise Ship Excursions