I'm good buddies with the tower controllers where I keep my plane (and where she instructs) one of my friends said that I should ask her out on the radio next time we're on the same freq. I could clear it with the tower controllers an have flowers or something for her when we land.
Any elaborate 'asking out' for the first time usually never works. Putting her on the spot like that would put her on the defensive instantly and be a huge fail. Also, flowers before you're dating is a big no no IMO. As part of asking out for the first time, even a bigger no no as they could be seen as a crutch. Like, 'hey look how sweet and thoughtful I am. I bought you flowers. Will go out with me? Pleeeeaaaase?' If she wants to out with you, it wont be because you bought her flowers, it will be because she want to go out with you. Flowers initially add nothing. Girls don't want sweet and thoughtful right away, they want guys that are just doing their thing, and if a girl fits into that, so be it. If you pursue too hard, or come up with an elaborate plan to ask her out, you'll be seen as desperate. Just my $0.02