Once you’ve met a man with money, perhaps the most ominous proposition is fitting into his social circle, his pastimes, and his expectations. What you do have on your side is, well, you. He’s made the decision to date you, which means he saw qualities in you he desired — and disregarded your background. Take advantage of that fact, but don’t screw it up by ignoring the pitfalls.
If you’re not really in love with him, cut him loose. If you’re disingenuous, he’s going to figure it out sooner or later. If you’re gold-digging, you’ll find yourself faced with a prenuptial agreement anyway. If you were just looking for a sugar daddy, you just wasted some of the best years of your life dating a guy that you didn’t love. In that scenario, he got the best of you, literally.
A lot of men with money will run background checks on women with whom they get serious, so if you have had problems with credit, or a criminal history, get it out there in the beginning. In this sense, honesty is the best policy, and it usually holds true for all relationships: he won’t be able to hold anything against you later.
He’s likely paying for everything, and doesn’t mind it, but picking up an inexpensive tab every once in a while shows him you notice it. The worst thing you can do is appear as though you’re dating him for his money, so if you at least show concern for the fact that he pays for everything. If you can, take it one step further and get a part-time job, or do some volunteer and charity work. This also shows you’ll make a good high-society wife.
Unless he happens to despise the sport, if you don’t know anything about golf and tennis — learn. If you have to take private lessons, do it. You need to hold your own on a court and course, even if you only end up in foursomes once or twice a year for business outings. If you don’t know what you’re supposed to do with your napkin when getting up to use the restroom during a dinner at a five-star restaurant, or which way to angle your fork and knife to indicate you are finished eating, watch as many etiquette videos on YouTube that you can. A wealthy man likely will not enjoy his girlfriend to embarrass him in public.
You’re going to meet his family and friends eventually, but don’t try too hard to fit in. Observe how they interact for a good while before you jump into conversations — you need a sense for how you will best fit into your role with them. You’ll look like a gold digger if your first foray into their conversation is which cut of large-carat diamond you prefer. If they start talking about a particular stock which did well, for example, don’t ask questions about how much profit they all made, instead, try and ask an intelligent question about the company itself. Side tip: learn how to smoothly avoid politics and religion, no matter how opinionated you are on the topics.