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My experience with artistic types is that they tend to be short on ego, at least as far as the finances go. Honestly, if Magpie made six figures and I could just focus on my music I'd be about as happy as it's possible to be.
When I started dating my current girlfriend, there was a bit of uncomfortableness regarding money that wasn't dissimilar to your situation. We actually both worked at the same job at the time, but since there was a commission based component to the wages I tended to make more than her. However, I was out on my own and she was still living with her parents at the time, meaning she had a lot more disposable income than I did. The net result was that whenever we went out she tended to foot the bill. I felt bad about it, but it wasn't any sort of macho ego thing -- it was more that I didn't want her to think I was taking advantage of her, or that I wasn't contributing my fair share. It sounds like your artist friend might be thinking along the same lines.
We've been together for two years now, and co-habitating for most of that time. She supported me completely when my health took a turn for the worse.
Honestly, if it's that big of a deal, why don't you just talk to him about it? You don't have to mention actual numbers, just tell him that you make enough money that you don't mind footing the bill for your dates, and make sure he's okay with that. If you're making that much, I imagine you're in some sort of professional position and he may have an idea already. Nobody's surprised to find out that a lawyer pulls down a lot of cash, for example.
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I wake up in the morning more tired than before I slept
I get through cryin' and I'm sadder than before I wept
I get through thinkin' now, and the thoughts have left my head
I get through speakin' and I can't remember, not a word that I said
- Ben Harper, Show Me A Little Shame
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