The Date Who Sabotaged His Career For Me (& Helped With Mine)

Welcome to 29 Dates, where we explore the weird, wild and sometimes wonderful world of dating — one date at a time.


I had just quit my job to go on tour as a standup comedian. It was the biggest professional achievement of my life but I couldn’t enjoy it because I was stuck in this horrible non-relationship with a guy who kept needing space.

After months of frustration, I finally agreed to give him space and left to go on tour in Alberta, Canada.

My friend Bill* said I could stay with him in a place in Edmonton (the capital of Alberta) as long as I was quiet at night because his roommate, Alex*, had a big exam for aviation school the next day.

He was tall, dark and handsome with an early 2000s Bieber sweep (it was flattering, I swear).

I got in from my flight and was just about to take an afternoon nap when the front door opened and Alex came home. He was tall, dark and handsome with an early 2000s Bieber sweep (it was flattering, I swear).

He clearly didn’t know who I was, and I stumbled over my explanation as to why I, a strange woman who had seemingly broken into his home, was about to take a nap. He laughed; he thought I was funny. He said he was just back for a moment and had plans for the evening but he kept lingering and chatting, until he casually mentioned he had missed his plans so we might as well keep hanging out. I told him it was my dream to see the rollercoasters I had heard about in West Edmonton Mall. He made fun of me, then said: “Let’s go, I’ve got my truck.”

After months of being neglected by the guy back home, I was swept away by how Alex was up for anything. He took me inside every single shop in the mall and then to dinner. He drove me to my first comedy show. Then my second show. We had endless things to talk about. It was like we had known each other in a past life.

Finally, I insisted he go home and study for his exam, though by then it was midnight and we had spent a solid 10 hours together.

Three days later, my tour moved on to Calgary and I got a call from Alex, saying he had failed his exam and had been discharged from aviation school. Did I want to get lunch? he asked. Sure, I joked. Just take a short three-hour drive down to Calgary and we’ll get lunch.

Three hours later, he arrived. We were driving into the Rockies in search of food when the guy back home called. I quietly let it go to voicemail, figuring a bit more space couldn’t hurt.

*Names have been changed

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