Gentlemen, I need some advice and tips here regarding older women. I know there are dating sites and other sorts of online discussions boards that are probably more suited for "relationship" types of questions, but heck I've been here long enough to come to know that despite all the car talk and grease-monkey jibber-jabber, many of you know a thing or two about the finer things about dating and women. Maybe there's something to be said about those who drive fine old Mercedes as having a refined knowledge of women, particularily older ones. Besides, a number of you here are well-expererince in life, so anyway without further ado....

Okay, so I have in the past posted about a mad work crush...I would say maybe three years ago was when I first made a random post about it because I had to tell someone. This was no ordinary work crush--it was a stupid, silly, and oh so hopeless crush on my "boss." I mean it was someone at the top! I know, stupid, but love (if love it was) is stupid. I put boss in quotation because she wasn't my immediate boss but rather the second in command and was my boss's boss and essentially the boss of everyone in the organization, which was a government one. For the three or four years that I was aware that I had a huge crush on her, I remained mature and professional and respected her and her title enough to keep this crush to myself. I didn't do or say anything that would get HR involved because I wasn't stupid However, over the years I sort of made an effort to put myself in front of her by communicating with her more, usually via e-mail about random stuff that we might have talked about in person. Of course, I also tried to impress her with my work, and she would give me praises. Nothing over the top. We really got a good rapport going. I so badly wanted to let her know how madly in luuurve I was with her but couldn't.

The opportunity came when the director announced her retirement via e-mail about a year ago. Wait--what? Retirement? How old is this lady, you're probably wondering. I think she is going on 55. Of course I was bummed but then I decided that I had better do something. I gave her a card wishing her well and stating that I'd like to keep in touch. I might have said that through e-mail. She agreed. And let's say that by then she would have to be utterly clueless if she didn't know I liked her...a lot!

So fast forward. We have gotten together two times already for lunch and dinner last year. We're probably getting together this Thursday for dinner. Now the "dates" are really spread out, so it's not like we've been getting together often. This upcoming date will be our third time to get together since her retirement. I've been pleasantly surprised that our dates were not filled with awkward silence. On our last date we stayed pretty long talking. I'm in my late 30s, and despite the age difference and not to mention social and economic differences, we really got along well and had much to talk about. I still can't believe we had gone out together. Who knew! But the thing is I don't know if she is being nice and friendly or likes me. Heck, I don't even have her number yet and really don't know how to get that without really knowing how she feels about me. They say older women know what they want and don't play games. If she has any sort of romantic feelings for me, do you think she would let me know? I feel like with this third date, I have to be more aggressive. The romantic in me wants to kiss her to see how she responds, or at least tell her how I feel. Would a woman her age even go out with a younger guy if she didn't really like him? I know deep down maybe it'll never work because of age difference and different life experience between the two of us, but I wouldn't mind having a relationship with her with both of us understanding that we can have a thing going even if it's just for now.

More questions later, but that's enough for tonight. Btw, reasons I like her is that she has a beautiful personality, sweet voice, sophisticated, and have I mentioned that she's HOT? She looks sort of like the Danish PM