There’s this song by Train called “Marry Me” that’s been playing a lot on the radio lately. The first few times I heard it, I thought it was just your typical mushy love song, so I’d change the station before listening to the whole thing. But one time I was in a particularly sappy mood and listened to it all the way through.

If you listen, you’ll catch the line “Marry me, if I ever get the nerve to say hello in this cafe.”

Dude wrote a whole song about this girl, and he hasn’t even gotten up the courage to say the first word to her. I thought that was pretty pathetic. And then I remembered about this time I did something eerily similar.

Two years ago, I was sitting in this very Starbucks staring at a blank piece of paper. I couldn’t help but notice this one girl, and before I knew it, I’d written her a letter.

I wouldn’t say it was a love letter really, but a letter nonetheless. I wrote all about how I wished I could come up with an excuse to talk to her, but how she’d probably just think I was creepy & wish I’d disappear. And normally, I’d file that piece of paper away in my bag so I could throw it away without anyone ever seeing it and that would be the end of the story.

But it wasn’t.

Several months later, on a road-trip to Nashville with a few new friends, it hit me that I was sitting beside that very girl from the Starbucks. We’d been hanging out for a few weeks and I didn’t even know it was her.

As it turns out, the idea of her was much more exciting than the actual her, and things didn’t work out between the two of us. But it was like God was showing me that things don’t always end up exactly how we dream they should. And that’s ok.

Seven years ago, I promised myself that by the time I turned 28, I would either have a family or I’d try to sail around the world. Seven years ago, I would have put most of my money on the having a family part.

But as the years have gone by, I’ve begun to realize how undateable I became after my first sailing trip. For a while, I’d tell girls I’d just met about how there were whole families with kids who lived on sailboats instead of in houses with yards and fences and stuff. How they spent all their time together sailing around visiting foreign countries, learning about other cultures, meeting other vagabonds.

Then I realized that all the girls heard was about how these crazy nomad people live in boats smaller than their kitchen back home in places that don’t speak English & how I thought all of this was exciting and charming but they thought it was the stupidest thing anyone could ever do ever.

So I stopped talking to girls about that stuff and I had a few chances at long term relationships. I was even headed towards engagement and marriage and forever with a girl, but in the end, I just felt like I was pushing her farther from her goals and dreams and she was pulling me away from mine. I understand the whole compromise thing, but I don’t necessarily think that both of you giving up all your hopes and dreams is how love is supposed to work.

I highly envy many of the relationships and marriages around me (my parents’ most of all), and certainly hope to someday experience that. However, I don’t plan on sitting around forever waiting for someone with similar dreams to show up so I can begin enjoying mine.

So tonight I’ll spend another February 14th here at Starbucks, working on ways to earn enough money to sail around the world.

And I’m perfectly fine with that.


Bo is currently living in Orange Beach, Alabama trying to come up with ways to fund a sailing trip around the world. If you’d like to be a part of the adventure, consider sponsoring a mile.