OP, your post reminded me of a young lady who I worked with 20 years ago. I went to her place of work as a consultant and ended up as manager for 6 months. The first time I saw her I couldn't believe my eyes. She was probably the most beautiful woman I'd ever seen, and it seemed odd to find her in this run-down business. I avoided even looking at her that first day because I was afraid I'd not be able to take my eyes off of her. She was 17 or 18 years younger than I too (45 vs. 27 or 28).
I soon discovered that she was also very bright and had a terrific sense of humor. And I discovered that she had a thing for me! Her boyfriend, who was about my age, was out of town working on his masters or phd, and she soon started asking me over for dinner, time after time after time. I always declined, as I didn't think it would be appropriate.
Then she and a co-worker asked if they could catch a ride with me to a neighboring city after I'd mentioned I was going there one night. I said sure. Why not? But when I stopped by the office to pick them up, the co-worker wasn't there. Something had "come up" and she couldn't go, but the beautiful office manager still wanted to ride along. What could I say? As it turned out, we stopped and had dinner before returning, and generally had a terrific time at dinner and during the long drive back. That was the beginning of a great friendship that turned into a little more. We started going out to dinners, lunches and breakfasts. I taught her how to drive a stick shift, we'd go for walks along a lake, sit and talk -- and LAUGH -- for hours. I was falling in love and didn't care if it was appropriate or not.
As it turned out, we never quite got together due to some strange circumstances, but we would have and even planned to for a short while. When I think of the few women I've loved, she's right there in my mind -- the one who got away. She contacted me on Facebook a few months ago. She'd had similar thoughts about me, I guess -- said she's often wondered what we could have had.
I'm just mentioning this because your boss could have the same feelings as I did but knows it's inappropriate to start something in the workplace. You could also use your wits to get something started if you really wanted to.
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