My days are kind of free I am a disabled vet, who works from home doing Pc work and training people Pc skills. Most of my work is done at night Leaving my days free. I am an out going person who likes to be doing something all the time. When not working I am sailing, motorcycle riding or just sitting back and playing music and playing around on my pc! I like reading and watching movies and going out to eat! I also love sitting in front of my fireplace drinking some wine and listening to music!
Well I would take my first date to San Francisco and walk around maybe go to a couple of stores and look around to see what she looks at and likes. Then go to the Warf and eat sea food or what ever she wants. If she has energy left and does not want to end the night take her to a club with live music!
That or if she just wants simple and short go for some Java and chat!