Date In The LYF is the new column at LYFSTYL where we share dating escapades, both epic and cringe-worthy from all sexes. Send us your notable stories via Twitter with #DateInTheLYF.

It was summer, it was hot, and as was often the case, friends and sometimes more than friends (we had kissed a couple times, alright)  were making regular weekend visits to Vancouver. During my University days I awkwardly attempted to navigate the strange area between “friends” and “more than friends” more than I should have, and so was the case on this “date”.

I had no idea what kind of “date” it was, but I had more than enough time to figure it out, and at the very least I could let her reaction to the bill decide. It was a plan, but it wasn’t a perfect one.

I had many plans for this “date” of course, almost none of which I followed, except for staying sober beforehand, which at the time was a noteworthy achievement. It was a start, a good start, and before I knew it I was on my way to pick up a cute girl for dinner and drinks.

So far so good, I thought.

Little did I know the plan had already gone horribly wrong.

As we sat down at the casual Yaletown bar I had picked out, I finally started to feel comfortable. Too comfortable. When the server swung around to take our drinks orders, I knew why.

Th awkward bulge of my wallet wasn’t in my back right pocket like it should be.

Maybe it’s in my jacket?

Nope.

Here comes the server, better come up with a drink order, and an excuse. Fast.

“Will she I.D. us?” I wondered to myself in a spare split-second, gauging how much time I had before I had to confess to my date that she was paying for tonight’s meal.

There’s only one way to find out.

“I’ll have a Caesar,” she said.

“I’ll have a Blue Buck,” I blurted out with the grace of a teen that has just placed his older brother’s identification on the counter.

“Sure, sounds great. And could I see two pieces of I.D. please?”

Well I guess I’m telling them both at once.

“Actually, make that a Coke,” I said before slipping into the abyss of a memory so awkward only fragments of it remain. It was at this point I admitted to my friend that I had forgot my wallet on the “date.” From this moment forward, my mind was a mess of guilt, shame, and awkward tension. The “date” wasn’t lost, but I was.

What followed was an attempt at self-deprecating humour so awful that the couple in the booths next to us must have been able to hear the “Chhhk-Ssssss, Chhk-Sssss” sound of shovel and dirt as I dug myself a deeper and deeper hole.

I tried to play it off, but with every quip it became perfectly clear that the biggest joke of all was the date itself.

Oh well, at least I might get a blog post out of it.