Ask Your Wingman – Jamaica

As I am laying on my porch today, trying to relive the vacation I just got back from in Jamaica, I wanted to share some things with you that made my vacation amazing without having to do much at all. So I won’t be answering questions from the mailbag this time, but continue to send your questions to thomas@tsbmagazine.com. I expect a lot more questions from peeps in college so bring them on.

It was my first trip back to Jamaica in 6 years. My family is from there and although I could have stayed with family, I decided to stay at an all-inclusive resort. Considering that I was staying with my older sister, brother-in-law, nephew and my mother, there wasn’t anyone that I could REALLY hang and party with while I was there. So I was on my own, which meant one thing. I had to create my own fun. Part of that was making new friends.

Here is one thing that you should think about wherever you are – especially when you’re on vacation. If you see someone you’d like to talk to, go and approach them. Chances are, you’ll never see them again, they are NOT going to blow you off (pending you’re not creepy), and if you do get rejected and there is any shame, you can leave it at the vacation spot. YOU HAVE ABSOLUTELY NOTHING TO LOSE.

When I went to the bar, I began talking with the bartenders, who were relatively young (around my age), and our conversation sparked conversation with other people at the bar. By the end of the first night out, I had made about 4 or 5 friends that I could hang out with while on vacation.

When it came to women, I feel as though when you’re on vacation, you should feel as though there is more room for mistakes because under the pretense of having nothing to lose, you can afford to make a couple errors. I’ll tell you what. The same thing applies when you’re back home. If a woman makes direct eye contact with you, she is telling you it’s ok to approach her. One night, a woman and I were exchanging eye contact throughout the night. I was having a good time with friends so I was in no rush to make a move. When I finally approached her, we ended up having a great time and spent a lot of our vacation together (with various extracurricular activities). There were other women who I talked to and made connections with but it all happened because I took action on a present opportunity. You need to do the same too, no matter where you are.

It’s not about being cool or letting her know how awesome you are. It’s about having fun and not caring about what could happen. You only have the ability to work with what IS happening at the moment and what you can MAKE happen.

Learn to spread your energy and your value wherever you are. People find that kind of personality infectious and they will gravitate toward you. I remember (for the most part – I had A LOT of alcohol while on vacation) every night I was talking with a different group of people. Some were my age, others were married couples that’ve been married forever, some had just got married, and so forth. I was listening to their stories and I was sharing mine. By the end of the night, people were dying to hang out with me again. And by the end of my vacation, everyone knew who I was at the bar. Bartenders knew me by first name and were taking care of me first (which helped my mother and brother-in-law get served a little quicker whenever they needed a drink). Some people threw a farewell get together for me on my last night. I even had people who were in the lobby looking for me when it was time for me to checkout and leave. It was one of the best true vacations that I have ever been on.

I am not boasting for the hell of it. These people were awesome and I plan on keeping in touch with as many of them as possible. I had an amazing time and these are the types of things that I have always taught my clients and blogged about incessantly. I hope you guys can take these tips and my experiences and make them your own. Whether you are in your hometown and know a lot of people or on vacation and know absolutely no one, you can make your experience an amazing one if you just let go, take some risks and live in the NOW instead of the future of POSSIBILTY and FEAR.