How do you know him, and when, and where do you interact?

At the office, but he does not work with me - kind of for me. We talk often when he comes in and sometimes on the phone - I have his cell number and he has mine - he's never called me but has sent me texts.

If he works "for" you, then you don't ask him out, and don't go out with him,

Eevn working in the same building as issues, but working for the other never ends well.

But if you won't take common sense, then you ask him out, what is it with women thinking the man has to come up with the ideas

Of course you may also just remind him of his mom

Your to old for him. No offense. And u don't date employees

I don't think its wise to date a co worker, especially a subordinate. That's opening a can of worms to satisfy lust, or attractions, or a simple crush. I know, you don't want to hear or see the downside of a failed relationship that hasn't started yet, but 40 is a bit to mature to not consider it, or give it rational thought.

I am hesitant to advise someone to ask out someone he/she works with especially if either party is in a position of authority. In this case, not only does there appear to be one person in an authority position, but an difference in ages comes into play, too. Would either of those factors cause an issue in your work place? For that matter, does your work place have any rules/guidelines about employees dating?

Thanks Fr_Chuck -
I think I will go to church on Sunday. Don't hate - it's rude. Woman do take care of themselves with healthy eating and exercise - I happen to look 30. Age should not be a factor- if it was a man who was 40...

HI Cat1864,
To clarify, we are not co-workers. He provides a service at my place of business. Why should there be a concern of ages - it's OK for man to date someone younger but not woman? I know he likes me and I like him.

Hi hallie78,
Not an employee and once again if I were a man who is 40, would it be OK?

To be honest, most of us have the same reservations when it comes to a male who is 40 and a female who is 26. Fourteen years can make a big difference in where two people are in their lives.

Personally, once a person is over 21 (I go for that age because of legal drinking age in the US), I have no problem with the age differences as long as both parties are aware of the challenges they produce. Such as with the case of an older woman who may want children but the younger man may want to wait or the other side is a younger woman who wants to settle down, but the older man wants to travel.

You say, "but he does not work with me - kind of for me." You go on to elaborate that he provides a service at your company. IF you did go out with him, how would that affect the working environment? Could it ultimately affect his contract with your place of employment? Could it turn into office gossip? Would it cause issues for you? What if it didn't go well?

Quite frankly, I don't know why you are asking about getting him to ask you out. It brings up issues of manipulation to me. Like you want him to be the responsible party for doing anything. IF you truly want to go out with him and have no reservations about accepting if HE asked, then why can't you ask him? If it okay for man to ask a woman out, why isn't it okay for a woman to ask a man out?

Your lack of clarity is confusing, and suspicious, but if he is an outside vendor who services your company, then ask him out, and why play games, since you are so well preserved and all. Age has nothing to do with anything, and if he has your number, and text address, then he has access. You wants some tips I have one, invite him on a date, because if age doesn't matter, then neither does gender, when it comes to dating.

Is he married, or have a girlfriend? Do you know anything about him?

If you're a cougar be proud, and go for it, but you don't get to put others down because you are vague.

Why can't you ask him out?
You are both grown and I would imagine if he wanted to go out with you, he would ask you.
Don't play games, just ask him out.

I'm intrigued. What kind of "service" does he provide at your place of business?

Honestly, I think at the age of 40, this really shouldn't be hard to ask someone out.

That's just my opinion.

Obviously, he won't ask you out because he would think why would he ask a 40 year old out. So you got to make the first move. ASK HIM OUT!