How do I approach this guy who is in his 40s, good looking, well off financially without seeming like the many other girls that have approached?

He is a professional guy and I'm sure has had his share of women throwing themselves at him. How would I go about approaching or giving hints that I'm interested without seeming like a gold digger or something crazy? I'm well set on my own I'm just younger than him hence my lack of confidence approaching.

Would he be flattered by an attractive younger woman approaching or should I let him be the one to approach?
How do I approach this guy who is in his 40s, good looking, well off financially without seeming like the many other girls that have approached?
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