One way or another, your boss needs to understand that there is no such thing as a free lunch. If your boss is intentionally failing to pay you back for the lunches, he is basically a bully.
At the same time, if he is unintentionally failing to repay you, that can be a different story. For example, he might be one of these global thinking visionaries for whom lunch money is inconsequential. Or, on a less favorable note, perhaps he is simply too self-absorbed. Either way, unless you take action, you are going to continue to feed him, and he is going to continue to feed you a line.
There are several ways to deal with this, the most obvious of which is to avoid going to lunch with him, or else doing so with others. At least in the latter case, you can spread the costs among the group. You can also go to lunch with him and have only enough cash to pay for yourself, assuming the restaurant does not take credit cards. Besides, if it does, why can't it take his?
The final strategy is to catch him in an upbeat mood, tell him you need his advice, and then describe the current situation. His response will give you some real food for thought.
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