Old Man Dilemma

So, I know that I am constantly saying that I want a Sugar Daddy who would just take care of everything for me - and give me a Black AMEX that I do not pay the bill on. But what I am supposed to do when a situation (not quite of this magnitude) presents itself to me?

Let me start here. Krug is someone that I work with - not directly, but in my profession - and we interact a fair amount. I have know since I was in my last serious relationship that he has had the hots for me. He has pursued, and I have always declined his advances. This has been going on for several years now. We remain friends, and colleagues, but it has never gone further. Bear in mind that he is married, with grown children, in his 50s and is successful. Not multi-millions successful, but well off enough.

Fast forward to a couple of months ago.

I was slightly inebriated one evening and sitting on the couch scrolling through my phone trying to find someone to entertain me. I happened upon Krug's number and decided to call him and shoot the shit with him. He told me he was out of town on business and then I recall saying something along the lines of "wishing someone would just come and whisk me away".

A couple of weeks ago he texted me out of the blue and the text message listed several places - New York, Las Vegas, Bahamas etc - and for me to pick one for my requested "whisk away". I told him that was sweet of him, but it was not necessary to do that. We exchanged texts for a little while and ended it with him telling me to pick somewhere and he would book the tickets.

Last night, he called because he wanted to know what my decision was regarding the trip. I told him I didn't know and that I had not really had a chance to decide yet. He reiterated that I could pick anywhere that I wanted him to take me, he would pay for the plane tickets, a nice hotel room and all of the expenses while we were there.

And then he followed up with: "How do you feel about fooling around with an older guy?" I told him that it didn't bother me all that much, but in hindsight, I am not sure if I could go there with him. He all but professed his undying love for me and told me he has always had a thing for me etc. Nothing against older guys as I don't typically date guys my own age, but I am not sure if I feel the same attraction with him that he feels for me. I feel as though if I were to go, I would end up doing something that I might not necessarily want to do, but would be a little more fine with doing under the influence of alcohol.

If I were to go, I would feel like I was taking advantage of him. Or if I did and ended up fooling around with him, I think I would feel cheap. Part of me thinks I should take him up on his offer and whatever happens, happens. But I also know that he is likely expecting something to happen.

I also worry about what this could do for our work relationship and where things would stand after the trip. But on the other hand, it could actually be a lot of fun, I could discover some kind of sexual attraction to him that I didn't know exists and a hell of a good time could be had from here going forward.

So, I am faced with an OLD MAN DILEMMA. And I do not know WTF to do.

Advice?


- Skinner

Sorry for the lameness

I was going to post regularly and then something called work and an election got in the way of things. So, to begin this post - which hopefully turns into a more regular posting - here is the inevitable Blogger apology. I am sorry for not posting, I have been busy, yadda yadda yadda...

I am in a funk right now. It is really a combination of so many different things that are going on. It's almost like a case of the PSD - Post Session Depression. (I work in politics and the legislature has a 60-day legislative session where we work and are going 90 MPH for the two months and then everything come to a screeching halt and it is a weird feeling of what to do now.) Don't get me wrong - I do truly enjoy my life and friends - but I just feel down right now.

Let's examine my life:

1. Home - never there. I travel too much for work and am never home. NEVER. I enjoy writing those checks each month for rent, cable and utilities when I barely even use them. Can you detect the sarcasm?

2. Work - I work too much. If you know me, you know this about me. I love my job, the people that I work for and with, but sometimes I just want a break from all of it. I want a day to go by where I do not turn on my Blackberry or my iPhone. A day where I do not check emails, text messages, PIN's, missed calls and voicemails. I am a little married to job and we are about to celebrate our three year anniversary.

3. Romantic Relationships - what's that? I am turning into the re-virginized Virgin Mary it feels like it has been so long. As much as I want to be in a relationship right now, my work and travel schedule wouldn't allow for a relationship that would be fair to the other person. I know this to be true, but sometimes it seems so hard to accept.

4. Friends - this is about the only thing that is always going well. My friends are the best - always there for me no matter how far away we all live from one another. LYMIDEC you all.

5. Family - can I skip this one? (Side note - I have been working on a post about my dysfunctional family and whenever it is finished, I promise to post...)

I just don't feel HAPPY right now. Yes...there are things that I do that make me happy, and I am still a smiling, happy go-lucky person...but overall, I just don't feel that overall happiness that we all strive to have in life.

Enough with the complaining. Things will turn and the funk will be over soon. I just needed to vent a little bit. I am feeling better already. More posts to come.

And although I know I don't have tons of faithful, devout, loyal followers of this blog yet, but what do you want to read about and see on here? I am trying to keep this somewhat anonymous - so face pictures are out of the question. But what about content? I need to find some stock photos to add to the blog to jazz it up a bit.

What do you think?

Skinner