The Biggest Tip You've Ever Given Somebody,....

probably not more than 15-20 at a restaurant with good food on like a 80-90 usd bill. cant think of any occassion where i would have tipped more than that.

You?

Don't put all your eggs in one basket.

This was years ago.  My friend, Rachel, and I went to this nice restaurant in Minneapolis.  I think it was called Palamino's, some kind of a horse.  Anyway, Rachel is super duper high maintenance with friends, but when she is in a position where she is to be the recipient of some type of service, her expectations get real lofty.  And when we were at a restaurant and our server was NOT a hot guy, well, Rachel could be a real See You Next Tuesday type.  Oh, she ran this waitress ragged, could not stop complaining, could not stop with the passive aggressive attitude.  As I can remember, the waitress was just fine, friendly and attentive, but it seemed like there's no pleasing Rachel...

So, anyway, our total bill ended up being around 120 dollars, for the two of us.  Rachel always liked to control every aspect of the situation and, thinking that Rachel was not going to improve her attitude by leaving the waitress a tip of at least 20% - when @ 15% is considered standard - I took it upon myself to leave the waitress a very healthy (not too excessive) tip of 30 dollars.  Rachel had treated the girl very badly and I thought she had earned every bit of it.  I slid it under the table, so to speak.  

Well, come to find out after we left, Rachel actually had left the girl the exact same amount for tip, so 30 + 30 became a 60 dollar tip on a 120 dollar bill.  I never told Rachel that I tipped her as well, but I bet the girl was pleased , and probably surprised, to have gotten the big tip.

Oh, you know, you are right, Toasted Cheese.  Rachel did have a big heart, no doubt about that.  It's just that she grew up in this tiny, redneck town in southern Indiana and she got treated horribly by most of the town citizens.   Everybody knew her.   Everybody.  The town population was around 4,000.  So, there was no hiding and Rachel was not the type to hide anyway.  That was one thing I totally admired her for and that was that she always stood up for herself and held her head high.  But I remember her telling me horror stories in high school when the kids would say really mean things to her, and push her into the lockers and trip her, slap her on the back of her head, awful stuff, really acts of violence and what made it so much worse was that the teachers stood by and watched it happening and never did anything to help her.  So, she developed a big chip on her shoulder and has never been able to fully let go of it.  Even when it was coming from a friend, somebody who truly cared about her, she was always on the defensive.  It's a shame.  

But, yes, there were many times when Rachel showed she had a very big heart.   And she was also absolutely hilarious.

I had to take a cab somewhere in a hurry and I think I just handed the driver $50 extra.
I didn't have time to fuss.

I'm not sure. When I tip I usually tip between standard 15% and 20% depending on the service. There have been times when I was with a large group where everyone contributed a little to the tip kitty in addition to whatever they owed. So I don't know of any overly generous tips I have left.

I have several friends who have worked in the restaurant business as well as my sister and they always tip. Sometimes they tip extra because they know the business. Some people don't tip at all, some tip only 10% to maybe 15%, others like me tip 15% to 20%, and then there are the very generous or those who are in the business that tip very well.

When you work in a serving type job, restaurant, retail sales, delivery service etc you have to deal with all kinds of people many of which are not very nice or pleasant to serve. That is one of the reasons people in the business always tip.