By: Jessica Kamikaze

My first attempt at arranging to travel on my own was in 2003. I was seventeen years old, had just started my first year of university and I had been dating my first boyfriend for a suuuper long time (one year). So, as a pair of super committed, super mature adults, we decided to go on our first vacation together.  I demanded that we go to a real live travel agent (it was 2003! I was scared of the internet!), but he wanted to book online. Clearly I should have seen that we couldn’t agree on anything and were destined for disaster, but I was young and in love! We went to a travel agent, paid the deposit, and broke up two months later…So long deposit.

Lesson: Unless you’re really, really sure, travel last minute.

After that, I was hesitant to undertake any real travel commitment with any of my subsequent Romeos. Or maybe that’s a lie. It was probably because every boyfriend I had after my first one was broke as fuck and couldn’t afford fancy trips. But I still LOVED them, cuz I’m not SHALLOW.  Also, because dating wealthy successful young men would make mumsy too happy and she needs to understand that I’M THE BOSS OF ME.

…Anyway, my subsequent travel was almost always solo. But then I was all like “Oooohhhh, I miss my boooyfrieeeend. I wish he could be here to experience this with me. He’s the only person who understaaaands meeeee.” So I usually had to suck it up and stop acting like a total wiener to enjoy myself, or mope around and have a crappy time (maybe because I was visiting my brother and had to watch him and his girlfriend be ooooh soooo in looooove! Like, noooo, don’t worry about meee! I’m not lonely and having a terrible time in stupid Calgary!)

Lesson: Don’t be whiney and dumb, unless you’re visiting your family and they’re not paying lots of attention to you. Then whine. Lots.

Then, finally, after several years of travelling alone, I took the plunge and booked a one week all-inclusive with a boyfriend who I was relatively sure I wouldn’t break up with before the trip (we lived together and the lease wasn’t up until long after the vacation! And everyone knows you don’t break up in the middle of a lease term). We booked the trip and it went off without a hitch. When we got there we bonded over so many things: Caribbean sunsets, sugary blended cocktails, and after all the beautiful wonderful experiences came the horrible, gut-wrenching, misery-inducing sickness. He got it first, on our fifth and sixth days and couldn’t leave the room. I got it on the flight home. ON THE PLANE. Have you ever puked on a plane? Then sat back in your seat, only to have to get up and PUKE AGAIN??

Lesson:  Don’t go to the Caribbean making big claims like “I never get sick, I’m not a weakling” or call sick people “baby belly” because it will only bring you a world of shame and grief when your curled up and crying on the plane.