There are Shouldn'ts and Shoulds

Sometimes Stephen Sondheim needs to write songs about my life.

Names have been changed to protect the fated.

Name of Date: Happenstance

Date #:1

Looks Like: Your outdoorsy flag football playing owning several dogs driving a jeep flannel boxer wearing type.

Occupation: Owns his own business making custom windows for different buildings. Apparently that is a thing. I mean obviously that is a thing, but who actually meets those people? Me.

Where We Met: So on my way to "Enough About Me" (which was one of my more popular posts. thanks so much fans and fanettes) I am getting off of the metro and heading up the escalator when I see Happenstance and very nonchalantly check him out. And by nonchalantly, I mean staring like he's not wearing any clothes. He's very attractive and chiseled and dreamy pants. I try not to be so obvious about my interest, but I can't help it. He notices and smiles and we begin some hardcore eye sex. Like my eyes were like "oh hey." and His eyes were like "sup" and then our eyes just stared making out in the middle of the room and dry humping each other while the other eyes around were like "gross."

So his literal eyes, not our metaphoric thrusting ones, follow me all the way up the escalator and makes me feel cute and desired and gives me confidence for the date I'm about to go on.

Which was obviously awful.

On the way back home I am upset that I wasted an evening and think "I should have just followed that guy wherever he was going." And lo and behold I pass him again as I'm heading down into the metro. I couldn't believe it. The odds are one in five billion. He sees me and just laughs and asks "did you plan this?" I can barely contain my glee and confirm that no, I did not stalk him. We chat for a brief moment before I hear my train coming and run to catch it. And like an idiot I do not get a number. All I have is first name.

On the train ride home my brain switches between the lyrics of "Moments in the Woods" and "Steps of the Palace." Because I feel like some sort of gay Cinderella. Cinderfella if you will. The way that movie SHOULD HAVE BEEN. Also singing Into the Woods to myself on the metro is one of the gayest things I've done. But feeling a cross between the baker's wife and Cinderella is a pretty damn cool feeling.

So what is our culture's slipper as pure as gold? Craigslist missed connections, baby. or grindr I supposed. For all you heteros... don't ask. (don't tell.) So many gay jokes! Regardless once I am home I check the missed connections and sure enough there is a posting for little old silly me. We exchange numbers and set a time to meet up for coffee the next day. Hooray sometimes the world is full of amazing moments and the starts just align and everything is right. That's when you know you're fucked.

What Happened: So the next day I'm all excited about our date and tell everyone about the amazing way we met. A perfect mixture of fairy tale coincidence mixed with technology's help. A modern parable.

As the day goes on we are texting and he tells me he has to have dinner with his sister so our date might need to end early. I am ok with this and impressed that he is close with his family because that is something I am not. I'm also grateful he told me and didn't just end things prematurely with me wondering what I did wrong.

When I arrive at starbucks we have about an hour of time before he needs to leave. I wait. and wait. and wait. After 20 minutes I call him to see what's up. Apparently traffic is so bad that he cannot find a parking space. So I keep waiting and waiting and waiting. By the time he walks in the door we legit have 15 minutes before he has to leave again. I'm annoyed but invigorated by the challenge to impress someone in limited time. It will be like a one round speed date.

We begin with the usual get to know you things. Happenstance is very kind and polite and communicative which I like and tips me off to the fact that he's probably older than I think he is. I don't mind this. Dating older dudes is the next step. If he's in his 30s that wouldn't bother me. There is a baby at the table next to us and he can't stop staring. He is enthralled by her, which I find adorable. I can tell he wants kids... and soon. Which makes me think... ok maybe mid 30s? I would be mostly ok with that. Suddenly I notice the beginnings of grey hairs on his temple. How old IS he? I begin to worry and come out with

"So is it rude to ask how old you are?"

"No. 42."

"I'm sorry I wasn't asking for the answer to the meaning of life. I wanted to know your age."

"42."

..............

I am on a date with a FORTY-TWO YEAR OLD MAN. I am that guy. I mean am I that guy? Have I transitioned to the point where I can no longer tell who is older than 30 and eliminate them from being considered? Am I resolving my messed up daddy issues. Am I SERIOUSLY out with some guy 17 years older than me who was already having sex with dudes when I was in kindergarten? In an instant the Sondheim song changes to "Hello Little Girl (Boy)."

It is time for him to leave. I am so grateful for the time constraint because I cannot wrap my head around the fact that the universe clearly wants me to date this guy. This very older guy who will be 60 when I am 38 and probably still very hot and good looking. I walk him to his car confused as all hell and wonder If I need to add "daddies" to my interests on my online profile. Again you heteros don't EVEN wanna know.

Gained Points for: Being polite and kind and respectable

Lost Points for: Looking 10 years younger than he really was

Mistakes I Made: Being agist? Is that really a mistake though? Sometimes dealbreakers are just dealbreakers.

Chances for Another Date: I am still on the fence about it

Overall Grade: B