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I mentioned that vacation boyfriend, Tom, actually saw me the night before he met me in the lobby. He heard me laugh, turned around, saw me and knew he was into me. Then he heard me say something about living in Chicago and he said right then he knew he had to find me. I called his bullshit but then he showed me a text on his phone to his friend that read something to the effect of… If you see that brunette from Chicago at the bar, text me and I’ll come down. Weird that he just knew, right?

I hung out with vacation boyfriend for the next three nights. We did not sleep in a room together again. Here is my reasoning, I like this boy. I am fully aware that we are in paradise, on vacation and this is NOT real life… but he is moving to Chicago so there is a potential for something to possibly flourish later this summer.

After I got home, he called me one day and asked if I could come back out to the island. I had told him there was a possibility that my department would be laid off and I would have a lot of free time and I would check. That night he sent me an itinerary with flights asking how these dates looked. I called my boss and asked her if she knew when my last day would be, she told me to take the trip and not to worry. So, I called him back and said book it.

And so, the adventure begins! Here I am writing to you from the flight, somewhere over the ocean. I will see him in 2 hours and my tummy is doing flip flops. I am so excited yet so nervous. I think it is going to be a good week though.

He is very sweet, so thoughtful and just a really nice guy. I do have a hang up though, he has a child. I know, I know… say what you want about me, call me selfish or whatever, but I am 28, childless and not quite sure if that is something I can take on. I told him this outright, too. I mean, I am sure for the right person I could get over the hang up. Luckily, he is recently divorced and the last thing he wants right now is a new relationship.

We both need each other right now, for different reasons. I am the first woman he has really clicked with since his divorce and, for me, well, I need someone who will treat me the way he does. On top of that, I really like him. We seem to have many of the same opinions, like the same things, read the same books, etc.

Side note, while I was writing this the guy in front of me just asked if I would lower my shade, he is a whole row in front of me and the window shade is directly to my right, it’s my shade. I get a bit claustrophobic and really like the natural light, plus I am working and hate nothing more than a dark computer. Who does that? Get a eye mask, I travel with one… it puts me right to sleep on a plane, plus it doubles for bondage.

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