I am still not sure how I get myself in to certain situations.
I know that I have a very deviant side to me that lacks a moral compass.
Maybe someday I will have to see someone about that.

Being that it’s summer and boating season is upon us, I am a much happier camper.
Even better when days at work become slow and I can sneak away from work to do a little lunchtime sailing.

It happened to be one of those days that contributed to this situation. I am still not sure how I get myself in to certain situations.
I know that I have a very deviant side to me that lacks a moral compass.
Maybe someday I will have to see someone about that.

Being that it’s summer and boating season is upon us, I am a much happier camper.
Even better when days at work become slow and I can sneak away from work to do a little lunchtime sailing.

It happened to be one of those days that contributed to this situation.
I woke up at my usual 5:30am feeling pretty good. After getting changed and having a sip of coffee I headed out for my usual morning run.
As I was running along I noticed how beautiful the morning was. The sky was clear and the sun was up doing it bit to warm the air.

When I finished my run and returned home, it was still quiet. My wife and kids were still sleeping off their late night of firefly catching.
I decided to head down to the basement to cool off from my run and check a couple of emails.
There were only a couple pieces of spam in my inbox, so I checked the weather to confirm what a great day it was going to be.
We were expecting 88 degrees with 18 knot winds. “This would be a great day to go sailing” I thought to myself.
Then I did a quick check of work and noted that things were pretty light. I made up my mind on what I was going to do today.
I decided, since I had some time to kill than I would go visit one of the old chat rooms that I used to frequent when I was single.
The room only had one person in it, which I did not recognize so I left.
I still wasn’t ready to start getting ready for work so I decided to drop in to one of the local public chat rooms.

I entered with my usual “Morning everyone!”

I got a couple of hellos back followed by the usual chatter in the rooms of people who are familiar with each other.

“Beautiful morning outside” I continued.

There was a “Yes it is” followed by a “Too bad I have to work” comment.

“True” I continued, “but I think I’m going to play hooky during lunch today and go sailing.”

That got a couple of responses that read “Lucky dog!” and “Sail some for me” and “I want to go!”

I was feeling pretty good about my decision as I watched the conversation scroll along.
There was a guy that asked me what kind of boat I had and where I sailed out of.
I told him I had a 36 foot Beneteau out of Winthrop Harbor.
He told me he had a 41 foot C&C that he raced out to of Belmont but that was too far away for him do any sailing over lunch.
I decided to wind up my chatting and closed out the chat room when I got an Instant Message.

“Are you really going sailing today?” it read.

“That’s the plan” I replied.

“Out of North Point in Winthrop Harbor?” it chimed.

“Yes” I replied, not really sure where this was going.

“Can I come?” The message asked.

I was a little surprised by the request. Very rarely do you get total strangers asking to go sailing online.
I did a quick check of the profile which only left me with a little unrest.
It just said she was female, her name was Amy and she was a student.
Then I had to ask myself, College, High School or Junior High?
I had a feeling I could get myself in to a lot of trouble if I wasn’t careful.
The chime from the IM brought me back to the present.

“Pleeeese, I really want to go” she pleaded.

I decided I would try to dissuade her from going and wrote, “I don’t know, I’m only going to be out for a couple of hours at the most.”

“That would be perfect! So I can go?” was the response.

I shook my head, not believing what I was reading.
I was about to write again when she chimed through again.
I looked over and ready then smiled a little in disbelief.
“Please, I really want to go. I’ll do anything if you let me!” it read.

My mind instantly slipped a notch when I read it. I was pretty sure I was dealing with a teen or just someone playing around.
I decided to play along a little and see where this was going.

“You should be careful saying things like that. You could get yourself in a lot of trouble” I replied.

The reply was a simple smiley face with a wink.

The next chime showed, “So does that mean I can go?”

I sat in front of my computer knowing I should just say no. But my gut told me I could say anything and this person wouldn’t show up.
I figured it was probably some 40 year old guy getting his jollies or something.
I decided I would let fate decide.

“Well, I am planning on casting off lines at 11am” I wrote.

“Cool, I’ll be there at 10:45” was the response.

“I’m Amy btw” followed.

“Bill” was my reply.

What had I just done? Did I really just invite a total stranger to go sailing; most likely a teenage?
Oh, my wife would kill me if she found out!

Then a thought occurred to me.
I quickly wrote back, “How will I recognize you?”

Her response was fairly vague, “I’ll be the cute girl with brown hair in jean shorts, a pink top and a bikini underneath.”

I looked around the room in utter confusion with myself.
My eyes happen to catch the clock and it was time for me to get going.
I sent one last IM to say I had to run.

“Cool, see you then” she sent.

I logged out and shut down the computer, and then I went upstairs to shower and get dressed.

“Nobody’s going to show up” I kept telling myself.

After my shower I put on my jeans and a button up shirt.