Dating in Paradise Is Harder Than You Think

Dating while sailing around tropical islands sounds like it should be easy… but the reality is a lot more complicated. When you live on a boat and cruise full-time, you are constantly moving from one place to the next. You are rarely in one place long enough to casually date, and most cruising destinations are full of couples, families, honeymooners, and retired cruisers — not single people looking to date. Then add YouTube into the mix. In this episode, I talk about what it is really like trying to date while living on a boat, traveling internationally, filming my life for YouTube, and dealing with the audience speculation that comes with every new woman who appears on the channel. We talk about dating apps, meeting people in cruising destinations, why relationships can move so fast on a boat, the difference between crew and dating, privacy, jealousy, and how hard it can be to know whether someone is interested in you, the travel, the lifestyle, or the camera. Dating in paradise is not always what people think. Download the Sailing Doodles Crew App on iOS and come join the Crew!

You can listen to Dating in Paradise Is Harder Than You Think online on Radio and Podcast. Open the player on this page to stream the available audio.

Dating in Paradise Is Harder Than You Think is an episode from Sailing Doodles Podcast by Sailing Doodles.

This episode is 0:34:50 long.

This episode was published on May 7, 2026.

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