Dunno about your female acquaintances by my girlfriends and I hate it when we're dating successful, prosperous men who aren't comfortable being themselves. Firstly if a man sticks to dating women who've generally only associated with successful men, one's money won't be an issue - it will be assumed. I tell my guy friends that all the time. I also tell them when they get all uncomfortable being themselves it screams to a "certain" kind of woman "I've dated gold diggers in the past who gave me drama so I don't talk about my wealth because it gets all funny" - that's a total turn off.
When a fellow demonstrates confidence and ease with his wealth and success it says -esp to a "certain" sub group of women - it says "I have a discerning eye and I am a good judge of character; I attract women with high standards but I am smart enough not to get played; that's why I don't get all antsy discussing my resources - it's like water or air or my Carnegie Club membership; it's there and it's impressive to some but I don't make a big deal about it...."
Having said that, Marquis Jet is running a Christmas special and the powder is wicked in St. Moritz right now, -mind as well get in that Christmas spirit with the Lady and get lucky (lol...j/k)
If she's socially ambitious and/or civic minded a donation in her or her family's name to her favorite charity would probably go over very nicely too (that's if she is not into material frivolity).....If that doesn't work, just email her your keyword list....