Do you think this guy is not assertive enough?

Anonymous
I went out with my crush and a few friends. My crush foot the bill first but he thinks that the cashier overcharged us. He told us about it but he didn’t really want to check with the cashier. So I just went to the cashier and asked for him. I thought that it was quite a simple task and it wasn’t particularly confrontational…
Do you think this guy is not assertive enough?
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