Seems to me there are three categories of pilots here:
1. First one the chauffeur. Flies somebody else's plane for a living. They even wear a uniform. NOT IMPRESSIVE! Not going to score boasting about being an underpaid bus driver/chauffeur/glorified taxi driver.
2. Second one the owner or renter of a smelly 35 year old pile o' junk as described by Stratobee. This is going to be a total turn off to a woman not interested in flying!
3. Third one and seriously under represented here other than yours truly soon
the owner and operator of something impressive. A plane with a real cabin where she can enjoy a glass of champagne and be spoilt and treated like the lady that she is. A plane that is fast, pressurized and can fly her above most of the weather and get her quickly to the destination she wants to go to such as Aspen not some nasty $100 hamburger joint, and allow her to arrive in style.