No matter how much money you have, there will be others who have more. If you live in a Park Ave apartment that you own and send your kid to a private school, she will inevitably have friends who live in entire brownstones, have a string of show horses, houses in Easthampton and Vail and private planes to get to them, and who accessorize their uniforms with Madison Avenue purchases (of which they tire quickly). So although you are actually remarkably privileged in the world, you feel like a pauper in your social circle. You can try to keep up (unsuccessfully) or just come clean. It’s awkward to say "I can meet you at the club but I can’t afford dinner at X tonight " but it’s important to learn how to do it with grace.