Great thread you started here Jim.
I'll preface my comments with; I was a busboy/dish washer in junior high and a waiter in high school, so I know a little about tips and tippers.
When I got all growed up I swore to myself that I would never be "That guy" who doesn't give a rat's ass about others. For the most part, I've been true to that.
I do believe that T I P stands for, "To Inspire Promptness" ( some think it's To Insure Promptness, but that's not what Insure means - so I use Inspire). And accordingly I have been known to regularly tip in advance.
Yes, I typically know - as most of us do - about how much a night out / dinner is going to cost, give or take, in advance of going out. Or, as some do, budget a specific amount for a night out (including tips) - does that make sense?
So, if I know about how much I'll be spending, I don't need to wait until the end of a meal to spend it.
If I enter a restaurant - no reservations - and it's busy, I break out the "Roll". I always tip in cash - servers love cash and it keeps the man out of their pocket.
When a place is busy, depending on the quality of the establishment, I'll slip the person at the podium a twenty (or a ten if it's a small joint) and tell her/him, Please do your best, we're famished. If we have reservations I don't usually do this, unless we are in a real big hurry.
It works 99.9% of the time.
Now, I'll get seated - if it's a fancy joint, yeah, I tip the Maitre di. Then the busboy comes by with water and rolls, etc. I'll many times hand him a ten spot and tell him to keep an eye on our table. I learned that move early on in my career as a busboy when the very same thing happened to me. Boy did that guy get good service from me that night! I always will remember that.
So, now that everybody in the joint is happy so far, I size up the waiter or waitress the minute they step up to the table. If I'm entertaining, I make a point to politely whisper to my server that I'll be paying and that he/she should take excellent care of my guests.....then I slip a $20 and say, "Here, this will get the ball rolling, keep the glasses full".
At the end of the night, the tip starts at 20% - it can go up or down, based on the service, the bill with or without tax or based on the number of times the server smiles - it's my party, I make the rules. If it's a big party and they automatically add 15% to the bill, I make a point to supplement that with cash directly to my server.
When it's just my wife and I, I pay with a card and tip in cash. Eff the establishment, they don't need to know how much the waitress got from me. Typically they have to fill out a sheet reporting tips, so I leave that to them to decide how much to put down.
Funny story - true too - recently took a party of twenty or so out to celebrate my wife's birthday. It was a blast, small place, but excellent food and the service was superb! Heck, I can't remember the last time we had so much fun.
When the bill came I handed our waitress the card.......she came back with that neat little leather folder and it was then I realized that I didn't have my glasses. So, squinting like a new born a figured out how much the tip should be and added some more until it felt right. I didn't have much in the way of small bills and my guests had pretty much all filtered out towards the parking lot.
The waitress was very happy that night I can assure you.
I'll leave you with this:
