Dating an older rich man
Banks, convention centers or coffee shops in business districts are the most likely places where you can meet rich men.
Maybe rich men are very busy with work, but you can wait for lunch or coffee time to chat up with them and who knows, maybe a date will be arranged.
Of course, dress your best, because first impressions are very important.
Like charity events, volunteering is also a great way to meet rich men.
Political organizations and events also attract ambitious, successful men.
Yeah, we might also have emotional baggage, but the more time we've had to date around, the more we know what we like and (hopefully) how to avoid making the same mistakes we made previously.
All right, so no one knows what they want, but we've got a job, if not a career, and some money saved up, because we already did that thing where you spend all your money and then have no money. We've learned a lot from our previous relationships.
Maybe you will not be able to afford to do shopping for yourself, but for sure you can meet or start to talk with a guy who does.
Start running your errands and doing your grocery shopping in upscale neighborhoods.