How to Travel the World: Leaving Love

Updated: Mar 13, 2019

He was sitting at a booth at Old Chicago, table number 21. He was alone, drinking a beer and eating a calzone. He had one of his legs propped up on the booth across from him. He wasn’t doing anything to distract himself from his lonely dinner. He wasn’t checking his phone and didn’t seem interested by the sports on the TV. Instead he just...was.


His hair was spiked, but not in an “I just put a mound of of gel on my head” kind of way. It fit him and fit the collage of tattoos that ran down his right arm. I had a crush on him from the first moment I saw him. My section that night was in back and his table was in front, but I took any chance I had to walk by him. I thanked myself that I wore my skirt to my shift that night instead of the ugly black pants I usually wore.

During one walk-by, I told him I liked his tattoo – a sun that filled the inside of his forearm. He thanked me, not paying much attention. He’d probably gotten that compliment many times. But hearing his voice made my stomach flutter.


I told all my friends at the restaurant about my crush, and we giggled and stared from afar. So, when I walked past table 21 and he was gone, my heart sank.


I felt silly for being upset about some guy whose name I didn’t even know, but I cursed myself for not doing something about it when I’d had my chance. The next hour dripped by. I was bummed that I no longer had a distraction from the slow night.


A while late, I went up to the host stand to bide time. I looked out at the windows at the front of the restaurant, and I gasped. My crush was back! He was now sitting out on the front patio with a guy and another girl. I was absolutely astonished. I felt like the universe had given me a second chance and this time I was going to do something about it. The girl he was with gave me pause though, it could easily have been his girlfriend and I wasn’t about to make a move on some guy with his girlfriend sitting right next to him. I told the hostesses about my issue and without a single bit of hesitation one of them walked right up to the table.

“Is that your girlfriend?” She said, directly to him. I could feel the redness creep into my face even though they couldn’t see me. My crush was totally taken aback.


“Uh no that’s his wife.” He said and pointed to the guy across the table. They all laughed awkwardly. Satisfied, she turned and walked back to where we stood at the hostess stand.


“I can’t believe you did that!” I exclaimed.


“Well now you have your answer!”


She was right. I no longer had anything stopping me. I grabbed a waitress book from the counter and on a slip of paper I wrote down my name and number. I tucked it inside, took a deep breath and walked over to him.


“Hey,” I stood over him at the table, he glanced up at me. “You should call me sometime,” I said quickly and with a smile, as I handed him the book. He looked up at me and as my blue eyes met his blue eyes I felt something shift inside of me.


“Thanks,” he said to me, taking the book from my hand. I turned on my heel and I walked away, my heart beating quickly.



I have always been a pretty forward person, but I had never done something like that before. It was minutes before my breath slowed down to normal again. I thought about what I had felt when he had looked at me. I didn’t think I was just being crazy, there was a definite energy between us in that moment. What I didn’t know then was that I had just looked into the eyes of my first love.


Like so many great love stories, the days and months that followed flashed by in a blur. He had texted me later that night. We started talking, sharing little facts about ourselves, each of us realizing we had more in common than we could’ve imagined. We began seeing each other on a regular basis and soon became inseparable. We were lost in a summer haze, falling deeper in love with each passing day. My heart yearned for him when I wasn’t around him, and swelled in size each time he kissed me. He was unlike any guy I had been with before and I saw parts of myself within his soul.


But the days we had to share with each other were limited, and in the back of our minds we both knew it. We met in June and I had a plane ticket to Bangkok booked for November. A one-way plane ticket that marked the start of a six-month backpacking trip around the world. We tried not to talk about it very much in the beginning, enjoying the time we did have with each other and not dwelling on the future. But, there was always a nagging voice in the back of my head cursing me for being stupid enough to fall in love with an expiration date on the relationship. But as we all know the heart is the one thing in your body over which you have very little control.


In the end of it all, six months of love couldn’t compete with six months of separation. We didn’t have enough time together to fully realize what a future with each other would look like. I was torn between wanting to have the freedom to explore the world fully while not wanting to let someone go whom I loved so much. But as I learned, having the best of both worlds is a reality that is hard to achieve.


Through it all, I discovered one of the most important things about leaving someone behind – don’t leave any strings untied. Don’t leave with uncertainty about what the guidelines of your relationship are. The in-between state in which we left our relationship when I left him is what caused so much heartbreak.



Although I can’t go back and fix the mistakes I made I can pass along what I have learned to others, and it is this…


If you are planning a world trip and you are in a relationship be sure of where your heart stands before you go. If you decide that you love this person, and that a month, six months, or a year, is not enough time apart to break your relationship, then stick with them and never question it.


But if you are un-sure about it – if you think you don’t want to miss out on the attractive foreigners and late nights of drinking in exciting new places – then break it off. Maybe you will be together when you return, but for the time being make a clean break and focus on what you hope to achieve from your travels.

We have many liminal states in this life. Many instances where being suspended between one state and another is just part of being human. But love, love isn’t meant to be in limbo for too long.


So, find where your heart is meant to be, whether it’s safely tucked away with your loved one at home, or soaring with you from country to country. Once you’ve figured that part out you are ready to board that flight and fly.


Read the first installment of this series: How to Travel the World: Saying Yes

Read the second installment of this series: How to Travel the World: Telling Your Friends

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