Why do you question his interest in you after he professes it and more importantly, would simply loosening the purse strings allay your doubts?
You must care about whatever money he has just a *little* bit. What if the guy makes minimum wage (or is a real estate “investor”), and can’t afford a really nice date?
Also, what you describe almost sounds like you require some sort of earnest money to be put up in the form of a nice date – “proving” his interest in you is “real”.
I think some women are conditioned to expect a lavish date as a sign of how much a suitor cares for them. If you’re of that mindset consider the relativeness of the “nice date”. For example, if your suitor was poor, a really nice date could be construed as a real sacrifice on his part to please you. Assuming the gentlemen has alot of money, what would a really nice date prove? Maybe casual dates are his way of making a meaningful connection with you.
If he really does care for you, he will have learned enough about you from your past conversations to eventually come up with something special, regardless of how much it costs.
As for the prenup, I would consider it as another form of insurance for my assets. At the outset, no one plans for their home to burn down, crash their car, or get a divorce. Not having insurance in the first two instances is considered very foolish, why not the third?
