I still remember my junior prom I went with a group of like 10 people (myself included) to this pretty expensive restaurant.
Of the group the bill was around 500 bucks, the guys were paying so we were trying to figure out the split since everyone had something different. I was the only person who got a salad with dinner (no more than 15 bucks) and somehow when I put in my share and "everyone else did too" we were still 80 dollars short of the bill itself, much less tip included.
After forking over the difference + tip I decided to pay attention to how much people were putting towards the bill in those situations or simply remember what people had and how much it was. Having a photographic memory and being pretty good with numbers helps. Haven't had that problem since then but it was absurd.
I think if you tell the waiter/waitress before you order that you'd like your bill to be split it's not a big deal. Having bartended I didn't mind when people came up and said they were paying separate. What annoyed me was when a group of 5+ would order different drinks, I'd ring it in together for the total THEN they'd tell me everyone is paying for their own and only one guy would tip.
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