How much can you spend on dinner/drinks each night before you start catching your engagement partner's attention?

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Reasonable and customary is the standard. You should not focus on "how much can I get away with". Eat dinner. Expense it. The expensive ones should be balanced by cheaper meals.

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I always go with if I would have any reservation explaining the charge(s) to him or her then it's probably not the right thing to put through. Budgets and expectations vary by market and client

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It's okay if you have one big night a week, but make up for it with cheaper dinners on other nights

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<50 total

Average <60

But then again it depends on where you are... if you are in NYC or LA, a bit more is okay.

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