February 4, 2014

Dear Darren,

What is the best place for a first date in Pittsburgh?

Joe, North Side


Hey Joe,

A first date is like that thing where dogs smell each other’s anuses when they first meet. It’s an audition for your anus. The location of your first date shouldn’t matter to you any more than the location of the dogpark matters to the dog when he’s snout-deep. Don’t trick yourself into thinking location matters. I don’t care if you’re drowning together at the bottom of the Allegheny with sterling silver cinder blocks tied to your feet; if she doesn’t like the smell of your penis, you are donezo pal.

If you have to pick a place, make sure it’s unique, exclusive or dangerous. You want to stick out. That way, even if the date is bad, she’ll tell her friends about it and one of them will be super into it. If you’re having trouble getting started, here are a few options to get you going:

1. Night-picnic on a tandem kayak

2. A concert of her favorite songs

3. Throw pennies off the top floor of the Cathedral

4. Dinner at a romantic museum

5. Burn up the dance floors in the South Side

6. A half marathon

7. Build-your-own FallingWater

8. Casino brunch

9. Bike jousting

I once had a first date on the Monongohela Incline with a buxom Monongohela Incline operator named Irene. Her shift had just ended when I entered and we struck up a conversation as we waited for the trolly. Her uniform clung to her feminine shape like a condom on a penis, and she spoke to me of the weather and Inclines. But it was clear what she really wanted to do. She wanted to crotch-wrestle me all the way down to Station Square, and I was about to make weight (like a sex pun).

When the trolly arrived, I held the door and beckoned her into the car so we could “share the view.” She sat right next to me. For a moment, Irene and I sat in hot silence as we descended, the ancient gears and erotic pulleys sliding us down-mountain. All was well and right in the world, two beautiful strangers bathed in city light, gliding asunder and steaming up the night sky with our genitals. I was about to make my move when suddenly, the car stopped short and sat suspended, mid-mountain, halfway down the Incline. It was unspeakably dangerous.

As I peaked out the window thousands of feet down the looming rockface, my heart began racing and my tear ducts emptied cathartically. Irene told me to “get it together” and swung into action. Cool as an ice cube, she telephoned her colleague up top and started mercilessly asking him what caused the car to stop. I believe it had something to do with electricity. Once she hung up, Irene assured me we’d be moving in no time and gave me her jacket. I wiped my nose and smiled at her, and she smiled back. That’s when I realized this was about to be the hottest first date ever.

“I’d like to kiss you,” I said.

Irene immediately started laughing romantically and pinched my cheeks between her elegant knuckles.

“I’m married, but flattered,” she said. However, I could tell that she was very aroused and was still super into it. The chemistry was electrifying, the circumstances were perfect for naughty, public sex. But maybe I needed to prove my worth first. Perhaps my weeping had stifled her libido and led to that flimsily laid marriage defense (though I often find a shameless spell of crying in front of a potential lover has the opposite effect. Crying is a form of bravery in sexual warfare). But seducing Irene was going to require a more nuanced approach.

“I’m going to break this window, jump down onto the tracks and climb back up to the top to get help,” I announced and started checking the windows for weak places to break the glass, winding up my fists like tiny boulders with fingers.

Before I could even smash the first window, Irene was begging me to stay, arguing that I’d kill myself if I tried to climb the tracks. “It’s basically a ladder, and what are ladders if not ambitious train tracks?” I countered. “What are train tracks but lazy ladders? They’re shaped very similarly.”

Despite her protests, I began cocking my muscular shoulders and prepared to knock the window clean off its hinges when suddenly the older gentlemen sitting next to us put me in a headlock and Irene grabbed me by the arms and wrestled me to the ground. They did not want me to leave.

We tussled, the three of us, a tumbleweed of limbs and flesh and warm elbows passionately churning in over itself like a pile of sleepy puppies. We rassled.

Just as the commotion was escalating, the Incline kicked back into gear and resumed its graceful descent down the mountain as though nothing had happened. We responded in kind, pretending we hadn’t just engaged in a primal three way tango of strangers. Irene and the old man unhanded me and encouraged me to “calm down.” I agreed and winked at them and we sat out the remaining leg of the journey in silence.

By the time we reached the bottom, all bygones had been begotten and we parted ways on positive terms. Irene called me a “wild one” and smiled a sexual smile and went to meet her husband for dinner at Bar Louie. The old man told me to “take care of myself” and shook my hand. I apologized to his grandson and they left.

The lesson here, Joe, is that a bizarre date is just as good as a good date. Where it happens, what happens when you’re there; these are just petty details. A first date is all about two people dipping their toes in each other’s lovepools and deciding if they wanna jump in. The location of the pool has nothing to do with it.

Irene and I never went on a second date, but I had fun and I lived to date another day. And isn’t that what life is really all about?