CONFIDENCE

I am a doofus. Maybe thats my problem. I have NO confidence anymore. I didn't think I was a negative creep but it seems that I am. Remember the whole thing about me having sex a few months back? Well, I blew that out of the fucking water.

I am trying to get a jump on bills and also be able to save some for my trip to Shenandoah. Anyway, I decided to shut my phone off for a bit while I put my money towards other things. I told this wonderful woman this and that I would have to contact or be contacted via email. She seemed cool with that. Well, I had sent her a few emails letting her know my schedule and when I was available. She never wrote me back. I kept writing. She finally writes back and tells me that she knew I was busy and had my son on days off but she wanted me to make more time for her. I responded by telling her that I was sorry but that's the way it has to be. She again seemed to understand but never heard from her. I would get man bashing chain emails and no personal emails from her. Well, this last weekend I didn't have my son on Friday and Saturday night. I sent her an email to let her know of my availabilty . I had given her more than a weeks notice of this information. I got another lame chain email and sent her an email asking that she either send me an email worth reading or take me off her list. She responded with: "Since you told me you did not have your son this weekend I've been thinking about inviting you up tonight. After reading this email I'm glad I did not. Thanks." Did I fuck up by sending this email? I don't think I did but who am I to say? The thing that really sucks is that she was talking about letting me try anal with her.

Now to where my confidence comes into question. I was married for 5 years and have been way out of the dating pool for a while. Hell, I wasn't even that sauve when I was a single guy. We have this new secretary at work and she is drop dead gorgeous. She is single, 21, and has a kid. By all accounts she is out of my league but then I think of my dating history and know that I am able to attract beautiful women. There is really no competition at work for her. All the guys I work with are married or old. She has been there for 2-3 weeks and gets a lot of attention from every guy there. It's only human. I have been playing the not interested card. Partly because I'm not. The water cooler is in her office and I will go in a few times a day and fill my water bottle and make idle chit chat. She seems to be loosening up as she gets to know everybody. She seems very cool and down to earth. Everybody says I need to try and "hook up" with her. She seems some what interested and almost waiting for me to ask her out sometime. I think I could ask her out but am not confindent enough to do this simple task. What's wrong with me? Will I outgrow this?

Yes, I did say that "partly" not interested in getting with her. So in a Nick Horny list I will tell you why.

1. She is younger than me. 21! I am almost 30 and not sure I want to get into something with someone younger than myself. Thats one of the reason I wasn't happy with my wife, she was so immature.
2. Not sure what I am looking for. Am I looking for just sex? Am I looking for a friend with benefits? Am I looking to get into another relationship?
3. Don't want to be part of work place gossip. I am not the kiss and tell type and wouldn't tell anybody at work whether or not I went out with her and especially wouldn't mention sex to them. Rumors run rampant and am sure my boss would be calling me into his office. It's not against my company's policy to date but I don't like my personal business being common knowledge. Not to mention, what if things go well and then go bad? I ghave to see this woman as long as I work there.
4. Rejection! yes, life does go on, but again I have confidence issue of late as it seems. Maybe rejection will help me become sauve. Practice makes perfect.

So there you have it! I think I will just play it cool and see how it pans out. Again she has only been there for a few weeks. I don't need to be freakin' her as soon as she walks in the door. So I think the playing cool method is the best way to go and see how it plays out. Open to any and all suggestions.

*****UPDATE*****

Well, I am now almost certain that I am not going to make it with this secretary. I was making small talk with her today and she is a "church going" woman. She will be there Saturday night and Sunday morning. I had made some comment about us going to hell and she replied, "I'm not going to hell! My savior and lord Jesus Christ will make sure of that!" I am pretty much an atheist and am guessing we wouldn't be compatible. Unless of course she wants to just have a fuck buddy. Keeping my fingers crossed.