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Can someone set me straight on how to deal with this guy?

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Question - (13 January 2009) 0 Answers - (Newest, )
A female United States age 41-50, *hiningmoonlight writes:

I have been speaking to a gentleman on the phone now for about 4 months. I met him through a co-worker. There are no set expectations between us because we are going to see where things may go. We do keep each other in the loop in terms of whether or not we are seeing other people. Both of us are not in relationships presently.

Okay, what is my concern.... this guy is hard to read. Sometimes we talk 3-4 times a week for 2 hours and then we go a few weeks without conversation. We have discussed meeting since December '08 but his schedule seems to be too full. First it was his occupation, he owns a landscaping business and had jobs to finish for the season. Thereafter, he booked a vacation and then other trips "crept up." I blew it off and determined we'd get together at some point.

I spoke to him yesterday and now he advised that we might be able to get together soon. Again, he is unavailable doing something....work and pleasure I think. I finally asked him if he was leading me on (I did this because our meeting seems to get pushed back each time.) He insisted he wasn't, he would love to take me out and see if we click. We do have excellent conversations and laugh a lot. I do like him as a person.

The other piece is that I also learned some information about him that I researched and it was true. He did have some issues a few years ago where he went to jail for resisting arrest, unpaid tickets and losing his license. The other things I haven't been able to confirm: He smoked pot as a teenager and still does now. He hires escorts for his personal needs. He got into trouble with the IRS for not paying taxes on his business. I did not confront him about everything but I did ask about the arrest. He flat out denied it at first and said it wasn't him. It was a person with the same name, so I gave specific details and he got defensive and explained what happened. I thanked him for opening up, I told him that I am sure it wasn't easy to do and that I didn't judge him for something he made a mistake on. He asked if I was still interested in him or this whole thing. He also advised that he "didn't promise me anything..."

Basically, I was rather silent and told him I was unsure. I acknowledged that he never promised me anything and I was in no position to judge him. I am not his wife, fiance or girlfriend, but I feel like if I have a legitimate question on something like this that we clarify it. I am opening up to this man, and I do not want to reveal all of myself at once. I don't want to be hurt or let down furthermore, I do not know where this may go. I guess this is part of dating...getting to know someone obviously but also determining if he is worth the time.

He really seems to want to hang onto this set up with me. I have kept asking him why and he says I am nice and truly enjoys our conversations and we have fun. Sometimes he doesn't answer me directly and asks me the same question! He makes me answer first.

Perhaps I am analyzing this too deeply. I am taking this dating thing slowly. I just need some insight on my approach. Should I just keep him as a friend and seek greener pastures? Should I wait and see where this may go? Am I wasting time on a man who may never find time to meet for the first time?

Thank you and I apologize for the long post.

View related questions: co-worker, escort, fiance

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