Friday, September 3, 2010

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

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