If you could invite Jimmy and Jane over for dinner, what would you cook?
I would try and find out what their favorites were before hand, but if that was not possible, Red beans and rice, conch fritters, margarita pie
Would you have it catered or do it yourself?
I'd do it myself
What do you think Jimmy would enjoy eating at your house?
Hopefully Red beans and rice, conch fritters, margarita pie
What kind of music would you listen to?
I'd let them select from what I have, which includes Sirius.
What kinds of drinks would you serve?
Boat drinks of course.

I've got a fairly good selection of stuff, including tequila and some really great rums. Hopefully they wouldn't drink up all my really good rum though, but then I guess that's the price one pays to hob-nob.
Would it be a formal sit-down or outdoors on the patio?
Well, I would probably be living on my boat by the time this would happened, so it would be in the cockpit or on the dock outdoors.
Would you take him out to a restaurant or entertain him at your place?
My place
Assuming you would not be completely awestruck in his presence, what kind of dinner conversation would you fathom?
Travel, airplanes, boats, old TV shows like Adventures in Paradise, life on the road, was Freddie of Freddie and the Fishsticks really Jerry Jeff Walker, Key West, the Caribbean, and I'd actually like to find out what Jane's take on all this is.