From Ramon Johnson,
Your Guide to Gay Life.
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So, you've gone out a couple of times and he agreed to pick up the tabs. His apartment is on a scale significantly higher than your pay grade can afford. He drives a lux auto (or maybe just a step above your own). Or, you may be the one in the baller seat, sort of speak, because he just lost his job. In either scenario, you've recognized that your finances aren't exactly equal, but you adore each other and are willing to stick it out.

During the courtship phase of dating, unbalanced finances get little attention, but it may eventually become a concern as the relationship develops—especially if either one of you has your ego attached to your wallet.

Break the financial ice by bringing up income issues early. Well, maybe not on the first date, but eventually as the relationship advances to the next level. Be open and honest about your pay check and savings. Let him know what you can and can't afford. There is no one right way to bring up the topic, so just go for it. Use a current bill (such as the restaurant tab) as the opportunity to start the conversation.