Wednesday night last week, I was standing outside a pub on Bloor St., waiting for my date, who said he was running about fifteen minutes late. It was crazy hot and humid and I was sweating like a pig, which is a horrifying situation for a first date. He had postponed our meeting twice already (strikes one and two), and his lack of punctuality was doing him no favours.

I talked to Stef. I checked my e-mail. I glanced up and down the street. I checked Facebook. I updated my calendar. I checked the weather. I considered playing my iPhone airplane game. Fifteen minutes my ass.

Finally, my phone rang. He was out of breath and asked me if I was outside.

"Yes. I said I would wait out front?" I replied.

"Shit. Okay, I'm upstairs. I walked right past you."


"Be there in a minute," he said, and hung up.

He came flying out the door, tall and bearded, and gave me an awkward hug.

"Sorry about that! I didn't think it was you. I thought your hair was different. It looked different in your pictures."

"Oh. Okay?" I said, not sure if I should take that as a compliment or not.

"Wanna head up to the patio?"


He took the lead through the door and up the stairs. Isn't it proper etiquette to let a girl go first? Anyways, I was a hot mess (literally) after the forever winding staircase up to the patio, and plunked myself down at a table, winded and slightly worried that my mascara was sliding down my face.

I ordered a vodka cran and he ordered a beer. I found out he works in loss prevention for a shoe company (and is underpaid. Ha, join the club!), was originally from Ottawa, just obtained his G1, has one sister, and likes photography.

As usual, I was analyzing him to death in my head. He was kinda geeky and awkward, hadn't dressed up at all (cargo shorts, a t-shirt, and sandals), and reminded me a little of Seth Rogen. He admitted to having a slight case of A.D.D., and would jump from story to story without any warning, ie. he gets attacked by birds on a regular basis and ran security for a Sex and the City event at a shoe store.

Around eleven o'clock, he suddenly announced that he had to get going, as his side of the subway line was shutting down at midnight.

"That's cool," I said, "it's late and I have to get up really early tomorrow morning."

"I hate to go. I'm having a great time," he said, and I just smiled back at him.

He asked the waitress for our bill, and when it came, I asked how much my share was.

"About fourteen dollars," he replied.

I handed him a twenty and he walked over to the bar to pay our tab. He returned and said, "Shall we go?"

No change? I was already unimpressed that he didn't cover my drinks, but if there was no change, I guess he had used my money to cover the tip as well? I found that so incredibly rude.

I hopped off the bench and down the winding staircase we went. He walked me to the subway station, and waited with me for my bus, which only took a couple minutes to arrive. He gave me a hug and headed down the stairs to the subway.

Exiting the bus at my stop, I called Stef.

"How'd it go?" she asked.

"Ummm…" I trailed off and she began to laugh. Apparently when I start with um, she knows the date was only mediocre at best.

I turned the air conditioning up, put on shorts and a big t-shirt, washed my face and brushed my teeth. I climbed into bed, Willow curled up with me, and I turned the light out.

buzz buzz

I turned the light back on and grabbed my iPhone out of my night table. The Cheapster had sent a text:

How many texts am I allowed before you block me? Lol (we had discussed the multitudes of internet crazies, including the Stage 8er's text-a-palooza).

Me: Haha, you're good so far.

Cheapster: Nice to hear, you are also good. Good night ttys.

Me: Night

I was confused…he liked me enough to tell me he had a great time and text me the same night, but not enough to be a little chivalrous and pay for at least one of my drinks?

My dad and brothers were horrified to find out he hadn't paid for me on the first date. Dad said, "You paid for the tip too?! You are NOT going out with that loser again!"

Haha, I love my dad.

According to the men in my life, a guy should ALWAYS pay on the first date. I informed them that 95% of the guys I went out with did NOT pay, and I am always surprised when a guy tells me to put my wallet away. I read an article on the Men's Health website the other day about how a woman automatically assumes a guy is in financial trouble or cheap if he doesn't pay on the first date, and I will admit, that's what comes to my mind as I'm forking over cash for my share of the bill.

What do you guys think? Should I expect a guy to pay or cut him some slack? And I'm only talking a few drinks here, not a five course meal, as I don't do dinner on the first date.

To my surprise, I haven't heard from the Cheapster since, which is also nice, as it saves me from the brush-off. Maybe it was my hair?


  1. EWW!! I would be majorly turned off. I always went in prepared to pay but never really thought I should, ya know. Call it old fashioned but he should pay for the first one...I'll get him the second time (if he's lucky to get that far hahaha!!)

  2. Anonymous9:25 AM

    I don't think a guy should feel obliged to pay, but it's a good idea to. I always do it, but that's just because I figure it ups my odds of first-date nookie. I'm not sure if that counts as chivalry.

  3. Anonymous8:12 PM

    I like to go dutch. But I don't really like the concept of "Dating" anyway. How about just hanging out and seeing what happens? Are we that attached to social conventions that things have to be defined as dates, etc?