I would most definitely pick her up in my 1995 Toyota Corolla. I would certainly vacuum the carpet and clean the interior (including applying a light dose of armor all on the dash). The car would be washed as well as waxed.

We would hop on I94 South, toward Chicago. Stopping off at the Mars Cheese Castle, I would offer her a selection of Wisconsin's finest. Topping it off with a Sprecher root beer of course; I would invite her to a contest of belching.

Back on the road, I would inquire her on her thoughts on history and philosophy, economics, business and life in general in the modern era. I would be engaging and thoughtful, and seek out her council on cloaks.

We would arrive at Alinea in Chicago for a sumptuous tasting most exquisite. The melon would be cold and the potato hot. Wine would swirl in the glass, unlocking it's bouquet, and I would entertain her with some of Virgil's minor works.

Afterward, a night of splendor and grace at the Art Institute of Chicago, followed by coffee at Intelligensia. Later on, the sounds of boots knocking at a sensible business class hotel (of which a deal could be had via Expedia).