Should friends date?

I'm an older guy who suddenly realizes he has deep feelings for a much younger woman. Of course, it's complicated. This person I considered my best friend. I have worked with her for about 5 years I guess. She has been dating a guy who was possessive and didn't appreciate her. I really considered her my best friend and she broke up with the guy and moved to another city to continue her education and live with her parents. And when she put in a transfer to her her new job, it really hurt me.
But before she quit we went to a movie and had a few meals together. We were going to go watch another movie one night, but she had to go see her parents before we did this. I had called her all that day to confirm our plans, but she never called me back which upset me greatly. When I did finally catch up with her she had a new cell phone and gave me her new number. Later on she admitted she was upset with me because I was being possessive but I wasn't- just upset because she never returned my calls.
Well we got over this and I actually went to her new city on a date, I suppose confirming in her mind that I loved her.
But from all this I get the impression that she knows I care for her and she is playing games with me. I know this woman likes me as a friend, and I wonder why now she is treating me as a guy chasing her now instead of her friend for the last few years.

I'm an older guy who suddenly realizes he has deep feelings for a much younger woman. Of course, it's complicated. This person I considered my best friend. I have worked with her for about 5 years I guess. She has been dating a guy who was possessive and didn't appreciate her. I really considered her my best friend and she broke up with the guy and moved to another city to continue her education and live with her parents. And when she put in a transfer to her her new job, it really hurt me.
But before she quit we went to a movie and had a few meals together. We were going to go watch another movie one night, but she had to go see her parents before we did this. I had called her all that day to confirm our plans, but she never called me back which upset me greatly. When I did finally catch up with her she had a new cell phone and gave me her new number. Later on she admitted she was upset with me because I was being possessive but I wasn't- just upset because she never returned my calls.
Well we got over this and I actually went to her new city on a date, I suppose confirming in her mind that I loved her.
But from all this I get the impression that she knows I care for her and she is playing games with me. I know this woman likes me as a friend, and I wonder why now she is treating me as a guy chasing her now instead of her friend for the last few years.

When you enter a business deal what is required to close the deal?
A meeting of the minds for both party's and mutual agreement. Do you think that your relationship has met that criteria? Because you go to another city for a date it does not confirm anything, but the date.
The whole romance or relationship is going on in your head and you have to communicate your feelings, but I suspect that you wasted five years by not speaking up so it maybe time to move on and find someone else?

Harvey7.

I'm an older guy who suddenly realizes he has deep feelings for a much younger woman. Of course, it's complicated. This person I considered my best friend. I have worked with her for about 5 years I guess. She has been dating a guy who was possessive and didn't appreciate her. I really considered her my best friend and she broke up with the guy and moved to another city to continue her education and live with her parents. And when she put in a transfer to her her new job, it really hurt me.
But before she quit we went to a movie and had a few meals together. We were going to go watch another movie one night, but she had to go see her parents before we did this. I had called her all that day to confirm our plans, but she never called me back which upset me greatly. When I did finally catch up with her she had a new cell phone and gave me her new number. Later on she admitted she was upset with me because I was being possessive but I wasn't- just upset because she never returned my calls.
Well we got over this and I actually went to her new city on a date, I suppose confirming in her mind that I loved her.
But from all this I get the impression that she knows I care for her and she is playing games with me. I know this woman likes me as a friend, and I wonder why now she is treating me as a guy chasing her now instead of her friend for the last few years.

In all honesty, I don't think your initial post sounded like you had been waiting in the wings all this time. The sense I got was that now that she's single, you suddenly started to see her differently.

I think one of two things is happening. Either she has sensed that your intentions are different than in the past, and she is reacting to you differently. Or, she is behaving in the same way as in the past, but because of your newly-recognized feelings you are reacting differently. (Perhaps a cancellation to see a movie is more upsetting to you when you think about it as a 'date' than when it was simply two friends hanging out).

I suggest you assess if your own reactions have changed. And, if you are interested in something other than dating, you need to make that clear to her, and let her decide if that feeling is mutual.

I don't think there's anything inherently right or wrong with dating someone who was formerly just a friend, but both people have to be on the same page - and you need to be honest with yourselves and each other. Otherwise it's just going to be awkward.

In all honesty, I don't think your initial post sounded like you had been waiting in the wings all this time. The sense I got was that now that she's single, you suddenly started to see her differently.

I think one of two things is happening. Either she has sensed that your intentions are different than in the past, and she is reacting to you differently. Or, she is behaving in the same way as in the past, but because of your newly-recognized feelings you are reacting differently. (Perhaps a cancellation to see a movie is more upsetting to you when you think about it as a 'date' than when it was simply two friends hanging out).

I suggest you assess if your own reactions have changed. And, if you are interested in something other than dating, you need to make that clear to her, and let her decide if that feeling is mutual.

I don't think there's anything inherently right or wrong with dating someone who was formerly just a friend, but both people have to be on the same page - and you need to be honest with yourselves and each other. Otherwise it's just going to be awkward.