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

My Own Medicine

Sometimes I'm just not in the mood.

Names have been changed to protect those without a chance.

Name of Date: Hopeless

Date #: 2

Looks Like: Imagine the skinniest guy you know, then take off 10 pounds. Blonde hair and the dreaded weak chin. Seriously I need a team of people around me at all times so that I never date a weak chinned guy ever again. I haz a pwoblem.

Age: 23

Occupation: Grad Student

Where We Met: Adam 4Adam.com (he had cleverly chosen a straight-on photo, so I didn't notice his intentionally hidden weak chin. I cannot be blamed entirely)

What Happened: Well our first date was super uneventful. I just went over to his place and he made tea and we chatted and I sneezed continuously because of his house cat. Hopeless was a nice enough guy. Very intelligent, good listener, but also very needy. I picked up on this immediately. I'm needy myself so I was tripping over the signs. Talking about the future, telling me how handsome I am (truths, but ploys nonetheless), and begging to see me again. I was literally a week away from moving to a different state, so anything meaningful was the furthest thing from my mind. However, I had gotten myself into this hot mess, I had to follow-through.

A few days before I left he called and begged me to come see him one last time before I moved. I really didn't want to. I had friends to see, packing to do, plans to be made. But he sounded soooo pathetic and I know that needy voice because I've used it 200 times. "Please, just, let's just spend one last night together and in the morning we'll say goodbye." Cut to me in tears sobbing on my knees in the street while his car pulls away. Has happened more than once. No lie. I feel a connection with his plea, so I reluctantly agree.

He tells me to stop by when he gets out of class and we'll watch a movie (Aka he'll try desperately to take my clothes off and get me to say the words "maybe we can make this work somehow.") WE HAVE ALL BEEN THERE. I don't judge him too harshly, in fact his insane infatuation is probably flattering? I like to be needed. I'm a 2 on the enneagram scale. Look it up. It's super enlightening.

When I get to his place that night he tells me that he is dog-sitting and would I mind heading over to his friend's place so we can walk them? Normally I wouldn't care, because I love dogs. But, it's already like 10pm. I just wanted to spend an hour with him, maybe make out and give him a thrill, and then make it to the bar to squeeze in some last hangouts with friends. I resign myself to the fact that the evening belongs to him now. I am committed. This is his gift. Of me. I suddenly feel bad for all the guys I've deemed assholes who must have felt this exact same way while indulging my crazy.

The dogs happen to be a dachshund and a rescue greyhound. The dachshund dashes out of the house the moment he opens the door, barks ferociously at me, and runs away into the night. The dog literally ran away. The metaphor is not lost on me. With the disappearing jingle of his collar so goes any chance I had of having an enjoyable evening. Hopeless tries to remain calm and asks that I stay with the greyhound while he looks for the other. I begin to compose an acoustic jason mraz-ish version of "who let the dogs out?" in my head. It is stellar. The greyhound is gorgeous, if dumb, and is content to let me feed it then snoop around the poorly decorated house. A mannequin wearing a read rain coat in your living room? I can't think of any reason that is a good idea.

Ten minutes later hopeless returns defeated. No dog. Fuck. I have to help him now. His lip is quivering and the responsibility of being in charge and failing had broken him. I see all this happening in his brain and I think "oh great. I know he needs to be comforted now. He will want a hug and a kiss and for me to tell him it will all be ok." Seconds later he wraps his arms around me and I have to suppress a groan. Am I this predictable to guys I date? I see now why I am so single. So so so single. I oblige with the kissing and comforting (albeit half-heartedly) and commence looking for this damn dog.

It is dark out. Poorly lit. And I just want to go home and watch musical theatre majors riff through classics during their recitals on youtube. That is all I want at this point. But here I am calling out in falsetto for a dog who doesn't know me and clearly doesn't want to be home. After about 20 minutes of fruitless searching I am ready to tell this kid to give up and call the owner. But by the grace of God a car drives by and in his headlights we spot the little fucker crossing the street. Hopeless scoops him up and tosses him inside. Mission annoyingly accomplished.

We drive back to his place and in his highly emotional and relieved state he wants to celebrate by sex. Not even this excites me. I just go through the motions and actually become quite frustrated. I want to finish. I want to go home. I don't like this kid. Again flashes of every guy I've hated for doing the exact same thing to me come to my head. I'm a terrible person, but it still doesn't change that I just do not want to be with him. I can only suffer through about 10 minutes of cuddling before I leave. I make a point to get out as quickly as possible before he can break into the rehearsed monologue he has about how awesome I am and how good he thinks we could be for each other. I want out before any messy pleading begins and I am left to have to break this kid's heart with words instead of actions.

I leave and get in my car furious with myself for being that guy I hate. Hopeless deserved a lot better than me. Working out my past issues by agreeing to an obligatory evening was a pretty shitty thing to do.

Gained Points for: Wearing his heart on his sleeve.

Lost Points for: Having skewed expectations.

Mistakes I Made: Thinking that indulging him would be good for both of us.

Chances for Another Date: He still texts and messages me all the time. I'm trying as hard as I can to be polite but clear about my interest. I do not think it will happen.

Overall Grade: D +

Prelude

Sometimes it's just fun to flirt.

Names have been changed to protect the obvious.

Name of Date: The Boy Next Door (not because of any connotations of that phrase, but because he was literally living next door to me for a while)

Date #: (0)

Looks Like: Your typical up and coming hot young actor

Occupation: Actor

Where We Met: My screen door was open one night and he passed by taking out the garbage and we said hello.

What Happened: Ok so what follows isn't a date by any stretch of the imagination, but it is an account of the flirting that took place over one night to lead up to our first date. I just wanna make that clear so that you know what you're getting into. I'm big on clear expectations.

I was coming home from work one evening, it had been a rough day and I was looking forward to hangouts with my other neighbors. We all knew each other and worked together so it was like a sad little campus of a neighborhood trying to relieve dorm life. "Oh man, I can come over and week can bake cookies and watch glee and drink wine and I'll complain about my roomies. Yay!" Seriously this happened like every other night.

So I am coming home and I see TBNT standing outside his place. I had always thought he was super hot, but he was way out of my league. Like he was an empty slot for hosting the oscars and I was Heidi Montag. Shit just ain't gonna happen. But admiring him from afar had been enough for me. Well he sees me walking up to my place and he goes "Oh. I am sooooo tired. and literally collapses on the sidewalk." I make some joke about how pathetic he looks and his arms reach out toward me. A few other neighbors are standing around and offer their hands to lift him, but he knocks them away and again stretches him arms out to me.

I have been chosen.

I walk over and lift him up off the ground, and he is limp in my arms. Head on my shoulder, putting all his weight on me. Ding ding ding ding ding. We have flirtations. He probably thought he was being subtle, but after years of playing the "I'm so tired, i just, could you just hold me, and i'll just, i mean, put my head right here" game I knew exactly what was going on. All suspicions were confirmed when he caressed my face and smiled a coy smile. This guy wanted it. He wanted it all over his personage.

He then asked what I was up to, and I mentioned that a few of us were going to go lay on the beach and watch the stars. He cautiously asked "should i come?" Haha what was I going to say? "No. but you can come to my place instead?" Actually I probably should have said that. It was pretty clear he wanted to come just for me. I felt fancy and wanted which is not something I often feel. His invitation was a given.

At the beach, there were 6 of us total. We lay down close to each other, but never touched. Crazy sexual tension passed through both of us and after 15 minutes of light chatting among the group he announced. "So who is going skinny dipping with me?"

legit.

I was not going to pass that up, so I got up and began undressing. He looked at me and said "Seriously?" and I said "Oh hell yeah. Let's do this." It was at this point I was annoyed that the rest of the group was there. If I'm going to get naked with a boy for the first time there are things I'd prefer to do that I cannot do in front of an audience. I mean I could. But I doubt they'd appreciate it. And if I'm gonna do that I'd like to get paid or at least have better lighting. The moonshine does not a porn set make.

Alas others were present so our nudity was communal and rather than sexual. His body was firm and tight. Nice muscles, phenomenal ass, mouth-watering perfection. Temptation personified. We ran into the water and romped like children. Horny frustrated children. We would wander too close to each other, arms sweeping in hopes of brushing skin. This dangerous game was clearly noticed by everyone else who just chose to not say anything, lest they burst the delicate dance of seduction. P.S. I am using this paragraph as an entry way into erotic novel writing. I am so good at writing sexy sentences. Something with a shirtless man on the cover with a finger raised to the lips as if making a "shhhhh" sound.

After we emerged from the water and dried off and clothed we set off back home to shower and head to a bar. I wasn't too keen on the bar idea but his begging me to come was an offer I couldn't refuse. I showered (alone) at home and hopped in my car. The others were walking there and I felt no need to get sweaty on the humid night. I just wanted to look cute and poofy hair is the opposite of that. I passed them about halfway there and rolled my window down to shout something sassy. TBNT noticed, immediately left the group, hopped in the passenger seat and shouted 'DRIVE!' before anyone else could get in.

Alone at last.

Awkward at last.

What do we say to each other now? "So how was your day?" No. I have just seen him naked and the fog of sexual energy in my car is making it hard for me to focus. When we arrive at the bar it is closed and I am secretly grateful. More time in his presence without being able to touch or kiss or work it out somehow would drive me crazy. Much like the Britney Spears song "drive me crazy." Or the Melissa Joan Hart movie "... Sabrina the Teenage Witch in Paris with the Olson Twins, maybe?" Or something.

When I finally get home I log on to the fb to stalk his profile and within 10 seconds he has fb chatted me

"hey"

"hey"

"fun night tonight"

"yeah"

"you have a great body"

"you too"

Cut to 15 minutes of us telling the other what we like about the other's body. This is basically cyber sex without cameras or mutual masturbation. This is a sophisticated and heightened type of flirting that began mere hours earlier. How far we have come.

I ended the conversation before it could turn sexual or weird and we made a vague promise to hang out with each other the next day.

Gained Points for: Unabashedly pursuing me

Lost Points for: Not knocking on my door that evening after the bar

Mistakes I Made: Being too eager to skinny dip. I shoulda kept it classy

Chances for Another Date: Undeniable

Overall Grade: A