Quite a while ago, about a year after starting the series, I ran out of first date stories to share. Okay, this isn’t entirely true. I have one story left. One first date story that was such an epic fail I knew it would have to be a three part post in Adventures in Dating. The date was a series of unfortunate events that lead to a first date story that continues to make everyone I share it with both cringe and laugh out loud.

I decided that this story is too good not to be immortalized on the internet and that today is the day I share it with my readers. Without further adieu, here is my most epic first date. Let’s note that I use the word epic and not worst. I must give the disclaimer that the date overall wasn’t bad and the guy was sweet. It was just the series of events that transpired were so ridiculous and hilarious that I will forever rank it the most epic. It was no Mouse Novel or Poor Man’s Kanye West, but you’ll love it just as much. I promise.

It was winter time and I was in the thick of my online dating experience. The spreadsheet was in full swing. I had a steller online dating profile and I knew how to navigate a first date like the back of my hand. This date fell on a Tuesday night in the Yonge & Eglinton (or Young & Eligible as its deemed) neighbourhood of Toronto. I tended to stick with dates closer to downtown or the West end but I was branching out.


We met at a bar around 7:00 PM and instantly I saw Sheldon. He was average looking and very tall. He was wearing what looked to be a Harry Potter-esque knitted scarf, but it was endearing in a nerdy kind of way. We hugged and sat at a table in the corner of the loud bar. We split a pitcher of beer (never a good idea for me since I never eat before a date and get drunk after one glass….hence the time I got drunk and went to Forever 21 after a date).

With the beer flowing, conversation was easy. He had a nerdy sense of humour (think: puns and quoting TV shows) that had us bantering back and forth. For some reason, the alcohol really hit me on this date and I ended up getting pretty drunk. I didn’t mind when he was talking a little too loud and quoting some random movie while people stared. I didn’t even mind when he brushed a stray hair out of my eyes. I knew pretty quickly on that it wasn’t a love match, but I had a great time anyway. Even though Sheldon was a bit quirky, he was fun and sweet.

It started to get late and I told Sheldon that I really should get going since I had a long subway ride back to my apartment. He insisted I stop by his apartment, which was just a few blocks down the street. Now Sheldon was sweet like I mentioned so I knew he wasn’t going to try any funny stuff, but I was confused as to why he wanted me to come to his apartment. I asked him and he just kept insisting that he wanted me to see it. Not wanting to hurt his feelings, I reluctantly accepted.

Stop by the blog next Thursday for part two of my most epic first date ever.


Written by Tracey