Two of two

[Dymoel40]

This might sound a bit strange, but please bare with me. I am an older male (41) who is single. I am a nice guy who gets along well with women of all ages. Sexually I have not been with many women and I have a shyness combined with poor self-image that keeps me from dating much. Lately I have been talking with a co-worker of mine who is a young lady of 21. We have spent many hours chatting online and have brushed some personal subjects. She told me about a short wild phase she went through a year ago and some of the details of what she did. Our conversations have seemed to me to be flirty and quite personal, however I have trouble believing she would be interested in more. I feel as if I am going down a road filled with landmines. I don't believe it would be a good idea to start dating, however I cannot help but feel flattered by the situation. Is there a way I could tell what she is thinking without just asking? And yes I am aware that many will think I am just a dirty old man chasing a young girl, thanks.

 

[KindaKinky]

You stated she's 21…which makes her an adult, so you're not that dirty. Secondly, if you want to know if she wants more you could have lunch together.

The only reason you should not pursue this is the fact you're coworkers. IDK if it's old prejudices, but I find there's a certain amount of tension that occurs between dating coworkers that tends to hinder productivity.

 

[SweetErika]

Why does it matter what she's thinking? You recognize (quite correctly) that a relationship would be a very bad idea for a variety of reasons, so enjoy the professional time you spend with her and leave it at that.

It sounds like your time would be better spent working on your social skills and self-esteem. If you do that, you can get to a place where you actually can talk to and date women (outside of work!).

I'm getting the impression that you're using what this particular woman might think as a bandaid when you really need to heal the gushing wound that is your shyness and poor self-image. I'm sure you know that deep down, too, so get to addressing the real problem instead of toying with distractions like this.

 

[silverwhisper]

i concur: it's a colleague and hence a bad idea.

as ever, erika's advice is superb. consider getting out and joining a group like toastmasters or something, which will likely pay dividends both professionally and personally.

ed

 

[A_Kefka]

I'm personally against hooking up with people from work, but thats becasue it could get messy at work if things go badly. As far as the age issue, if you are both ok with it, I'm of the opinion that it only matters if you are looking for a long term very serious relationship.
Big age differences would be problematic if you were looking to start a family, or just be together for a long time romantically. But if you are both just looking for something physical and friendly then I don't see it making a difference. Of course shifting desires can be an issue (say she wasnts something just physical now, but later decides she wants a family) and how those things are handled could cause trouble, but thats a risk with any relationship.

 

[thirty]

This might sound a bit strange, but please bare with me. I am an older male (41) who is single. I am a nice guy who gets along well with women of all ages. Sexually I have not been with many women and I have a shyness combined with poor self-image that keeps me from dating much. Lately I have been talking with a co-worker of mine who is a young lady of 21. We have spent many hours chatting online and have brushed some personal subjects. She told me about a short wild phase she went through a year ago and some of the details of what she did. Our conversations have seemed to me to be flirty and quite personal, however I have trouble believing she would be interested in more. I feel as if I am going down a road filled with landmines. I don't believe it would be a good idea to start dating, however I cannot help but feel flattered by the situation. Is there a way I could tell what she is thinking without just asking? And yes I am aware that many will think I am just a dirty old man chasing a young girl, thanks.

I guess you have enough experience to judge if she is in that mood or not by not asking her directly.

We can feel it.

 

[surreality]

i concur: it's a colleague and hence a bad idea.

as ever, erika's advice is superb. consider getting out and joining a group like toastmasters or something, which will likely pay dividends both professionally and personally.

ed

I agree with this 100%. Take it from someone (me) who has had a work relationship gone terribly wrong and just don't do it. I'll quote an old proverb "don't shit where you eat"

 

[kindashy]

She might have a friend who could use a boyfriend...

 

[mississippiGuy]

I agree with this 100%. Take it from someone (me) who has had a work relationship gone terribly wrong and just don't do it. I'll quote an old proverb "don't shit where you eat"

amen.. work and playing around is just bad.. been there done that.. didnt end nicely..