Hello Captain Awkward,
I have an issue that you probably don’t get every day. I have a problem with wealth and dating. I’m in my late 20’s, and I have had the good fortune of becoming quite wealthy. Unfortunately, I am having trouble finding women who like me for me and not my wealth. Back when I was a poor student, I never thought this would be an issue, but it is. I believed that money would solve all my problems with being awkward and feeling inferior and not being able to get laid, and it did help with a lot of those things. It has made finding actual love and good relationships much more difficult. I don’t fit in with the dynastic wealth crowd, and I know there are tons of great women who grew up with money and are not in any way impressed by mine, but I just don’t fit in with that group of people. I have been trying to figure out how to navigate this issue, and it just blew up in my face.
I was seeing a woman for 3 months, but I was lying about my wealth. I have a small apartment in the same building as my real apartment, so I can try to get to know women without getting entangled with the ones who are just with me for my money. It is the sort of apartment that says, “I’m doing well, but I’m no rich guy.” Last week, I decided to come clean, and it did not end well. It was the first time where we went out and I was living life as I live it when I’m not worried about what people are going to think about my money. She thought it was this special occasion because everything was stepped up considerably from our usual dates. I tried explaining that really, I was maybe not being so honest about my income, which she didn’t believe until we came back to my actual apartment. She was furious, and I can understand it. She went on at length about my deception, not trusting her, and treating her like a potential gold digger.
It is true, but I don’t know what else to do. She won’t talk to me, and I think our relationship is probably over. How can I find people who like me for me while living a lifestyle that clearly shows how wealthy I am? I have been burned before both with friends and girlfriends who I thought liked me for who I am but turned out to be interested in being close to someone who is doing well. I have reined in my conspicuous consumption a lot in the past year and a half, but I like having a very nice apartment, I like dressing well, and I like having a nice car. I feel terrible about feeling sorry for myself because this is a problem almost everyone would be envious to have, but I am very lonely.
A Good Problem Is Still a Problem