LOL that's pretty good stuff..
But you also make some good points. It's the "Cash McMogulson" effect (I hope some of you have had the chance to read his chronicles.....if not......google them). If its a one night stand with say... a couger... then your gonna want to put on your rolly YM or sub... something that she will recognize and immediately associate positively with (we hope!!).
On the other hand.. if its a nice lady, like say someone your mom set you up with (don't ask) then you might want to go with something a little more restrained like a FA Jones, Porto, etc.
If you don't want to start with a lie, like crystalcranium said, start out with a gen....however, I don't consider wearing a rep a lie. It's just a matter of taste.
I personally, on a first date, would wear this:
In all seriousness.. I'd go with the Omega Chrono. Not because of the date or anything, but just because its my favorite watch!!