I've had several, but this one's my best:
About 20 years ago, I formed a couple of partnerships for the purpose of investing in properties owned by the RTC and by REO departments of busted banks and S&Ls (of which there were many in the late '80s). In connection with that, I had the occasion to meet with the CEO of a small, closely-held company in Dallas who was eager to invest in distressed properties. I'll call him Jerry (not his real name).
Jerry had a very attractive thirtyish administrative assistant whom I'll refer to as Deborah. She and I had a couple of friendly chats when I was waiting to meet with Jerry, who tended to be tied up with phone calls and late-running meetings. We talked about local events, movies, restaurants, etc. She even told me about a place she was dying to try. I thought she was trying to give me a little "hint, hint", but wasn't sure -- and, in any event, just to make both of us more comfortable, I wanted to wait until my series of meetings with her boss were over before asking her out.
About the time I had my last meeting with Jerry, he told me that Deborah had asked whether I was married. She also told him she thought I was very good-looking.
[Short intermission to allow any ladies who have actually met me to stop laughing.]
Having been given some obvious encouragement, I decided to call this very attractive and personable young lady and ask her out. As I recall, it was a Tuesday afternoon around 4 when I placed the call. I intended to ask whether she would care to try out the previously-mentioned restaurant Thursday night.
The person who answered the phone told me Deborah was on another line and would call me back within a few minutes. When she did so, I was on the phone and my assistant took a message. By the time I returned Deborah's return of my initial call, she had left for the day.
In the meantime, I was an occasional customer of what might be described as an upscale UTR agency. The owner had recently told me about a new girl she described as gorgeous, 32, 5' 6", 120 lbs., brunette, all-natural C-cup, well-dressed, personable, and intelligent. Sounds perfect, I thought. So I made an appointment for 9 p.m. that Tuesday night; the very day I had tried to get in touch with Deborah.
Finally the clock struck 9.
Guess who showed up!
Needless to say, we were both rather surprised. Deborah almost looked like she was ready to faint. After a minute, she asked whether I wanted to go through with the appointment. I said, "Of course!"
I had an absolutely great time and saw her many times over the next year or two.