Damsel in Disasters

A Romance column with Chelsea Tremblay

You can’t always tell when a disaster date is about to happen. Sometimes it starts off with a cup of coffee, some laughs, a walk through the Common, and then falls apart on you unexpectedly. And other times you can just feel the ominous air around you as you grin and bare it, thinking about how you’re definitely going to write about them later in your column.

That was Paul.*

Paul taught me a few things about dating. First of all, if your first date is on Yom Kippur you should probably find out if your date is Jewish. Or they should, I don’t know, maybe give you a heads up that they’re fasting. So when I showed up ready to grab a bite before seeing Ernest Shackleton Loves Me, I was sorely disappointed.

Grab a drink? I suggested.

Doesn’t drink alcohol.

Grab a cup of coffee? I asked, a light of hope in my eyes.

Doesn’t drink coffee.

So we waited outside Paramount for Shackleton to begin and this date be closer to ending.

We had front row seats to the show and I spent the night laughing while Paul sat stone faced next to me. The show focuses on a single mother who finds hope in life after meeting Ernest Shackleton on a dating site called CupidsLeftovers.com. At the mention of online dating I got an awkward smirk from Paul, because we surely were cupid’s leftovers, but I spent the rest of the show falling for Wade McCollum (Shackleton) instead of who I was supposed to be falling for.

Ninety minutes later, the two performers bowed to the audience’s standing ovation and I planned my escape route. I had to run home for an interview, it should have been easy enough. As we left the theater I mumbled an explanation.

“Sorry to cut this short it’s been nice but I have to run home and I’d invite you but maybe some other time we can..lunch..tapas..thanks...great show..text you..get home sa-” “I’ll come.”

Horror washed over me as I accidentally brought home my awkward first date. Second thing I learned from Paul: never politely offer anything you don’t mean. Because for the next two hours he sat in a beach chair on my porch (after crashing through a broken metal one, at which he looked mortified and I laughed a little too much) listening to me be interviewed about my life story. Shockingly, he still texted me the next day after hearing it all. Although between you and me, I was hoping he wouldn’t. The best part of the interview:

So tell me about this new column you’re writing for Your Mag?

“Ummmm ahhhhhh it’s ahhhh….”

It’s about online dating?

*wide eyes* *low key head shaking* *glances at Russell*

Oh perhaps we’ll talk about that some other time.

*Names have been changed.