A couple of years ago my best friend was moving from Ontario to British Columbia and I had the great idea for us to road trip it out there together. One last adventure before we were living 3,716 kilometres apart. Turns out life got in the way and after two weeks of concerned parents, booked flights and a funeral, I left by myself to meet Kelly out there. This is what happened. And what you can learn from my, ahem, shortcomings.

Pre-trip

11:59 p.m. Halloween night at the club. After a bottle of wine with the roommates while getting our costumes ready, and another bottle at the party, I’m now at the bar telling everyone about the amazing road trip I’m about to take. For some reason I keep getting a lot of: “Really?! You’re actually driving across Canada by yourself when it’s almost winter?” In hindsight, this might have been a sign that this was one of my more questionable life choices. But in my head I was a genius. A pilgrim about to explore and conquer the wilderness! Yeah… right.

Day 1

7 a.m. I’m wakened to my roommate pounding on the door: “Wake-up, it’s time to go!” I probably shouldn’t have had those last few shots at the bar. Guess it’s time to pack! According to my schedule (which only included the first two days) I had to be on the road by 8:00 a.m. to make it to Sault Ste. Marie by nightfall. I throw any clothes I can find in my suitcase, grab my toothbrush and deodorant and run out the door.

8 a.m. I’ve now been on the road for a whole 20 minutes before I realize my suitcase might be a bit light. I didn’t pack a jacket, boots, my passport or wallet… but I did remember all four bathing suits I own. Thank god. I turn around and grab what I forgot. Get back on the road.

Lesson #1: Pack the night before… not the morning of.

9 a.m. This is the greatest idea I’ve ever had. I’ve never felt so free. Don’t have to be anywhere, go to any meetings, answer to anyone. The morning radio talk-shows are starting so I start the epic road trip playlist. Oh wait… turns out the only CD’s I have are the new Macklemore album (which wasn’t overplayed yet), the new Ellie Goulding album, and a couple mixtapes from my high school days (but it is way too early in the road trip for “Cute Without the E” and “Sic Transit Gloria.” Okay, it’s never too early for Taking Back Sunday and Brand New).

Lesson # 2: Plan your music wisely. It’s way more crucial to a great road trip than you might think.

1:30 p.m. Seventh time listening to “Thrift Shop.” Still awesome. I’m a few hours past Peterborough and the regrets of last night are starting to come back. Time for greasy food. This is exactly why god put McDonalds so close to the highway.

6 p.m. I have been listening to Ellie’s album on repeat for three hours. We finish each other’s sentences, so we’re basically married. Finally arrive at my swanky digs for the night—the Super 8. According Eileen, the nice lady at the front desk, the 8 stands for 8 stars out of 10, so you know it’s legit.

8 p.m. I’ve showered and ready for a wild night on the town. On Tuesday nights, according to Eileen, everyone goes to the local movie theatre. So I spend my first night of freedom with a bunch of teenagers watching Ben Affleck rescue some journalists from That 70s Show from a bombing (I stayed awake for the first 20 minutes of Argo and made the rest up, but I’m pretty sure that’s what happened).

10:30 p.m. After this exhilarating day of driving, imaginary marriages (never say never), and Ben Affleck saving Eric Foreman, it’s time for bed because I have a good 13 hours of driving tomorrow. And thanks to Eileen, I’m only 75% my bed is bedbug free.

Lesson #3: The 8 doesn’t stand for 8 stars out of 10… And avoid the top blanket at all costs.

This is the first post in a series documenting my attempt of a cross-Canada road trip. I’ll have updates every few days, so keep an eye out for more stories of broken cars, life advice from Liz (Kelly’s mom), border patrol scares, and Eileen… just kidding, Eileen stayed in the Sault, but we still Skype once in a while.