I just had the most awkward situation at lunch! Met a friend of mine at a casual burger place in NYC. When we sat down, she asked for separate checks (which is fine). When the bill came, mine was $16.xx including tax and I'm sure hers was pretty much the same. I threw down $5 for a tip and she had an episode -
Friend - "Is that for my tip too?"
Me - "No, but it can be." (I throw down $3 more).
F - "that's too much!"
M - "It's fine, I don't mind."
F - "No, it's too much!"
M - "No, it's fine. A few extra dollars in the waitress's pocket is much more meaningful to her than a few extra dollars OUT of my pocket."
F - "I still think it's too much!" (But she gives up and walks towards the exit)
There was a definite pall between us as we parted! Should I have reduced the amount of the tip to make her feel better? FWIW, what I said to her above is my philosophy on tipping - I'm at a point in my life where I can be a generous tipper and the value of those amounts to me is tiny compared to the value they have to the waitperson that gets them.
Do I stick with my philosophy, or in my opinion, "stiff" a waitperson so a friend I'm with doesn't feel bad that she can't/won't tip the same way?
Jane
Friend - "Is that for my tip too?"
Me - "No, but it can be." (I throw down $3 more).
F - "that's too much!"
M - "It's fine, I don't mind."
F - "No, it's too much!"
M - "No, it's fine. A few extra dollars in the waitress's pocket is much more meaningful to her than a few extra dollars OUT of my pocket."
F - "I still think it's too much!" (But she gives up and walks towards the exit)
There was a definite pall between us as we parted! Should I have reduced the amount of the tip to make her feel better? FWIW, what I said to her above is my philosophy on tipping - I'm at a point in my life where I can be a generous tipper and the value of those amounts to me is tiny compared to the value they have to the waitperson that gets them.
Do I stick with my philosophy, or in my opinion, "stiff" a waitperson so a friend I'm with doesn't feel bad that she can't/won't tip the same way?

Jane
I am a generous tipper as well, and if I feel the service is worth I will definitely add a few extra dollars. I used to be a server, and I remember a few extra bucks on a tip making my day, and meaning a lot my income at the time. You do what feels right to you, and don't worry about what other people think.
In this instance, if I care about the person and want to calm that little self-doubt feeling, I find it's best to just say, "well (what you do) is okay too" without excusing my choices.
. we live quite a distance out for pizza delivery but they still come to us. so we usually tip $5 to the drivers. I have heard from some that they fight over who is going to make the drive to us b/c of the tip
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I also noticed that I get special treatment at the places locally that I frequent, extra donuts at DD, "forgetting" to charge me for ice cream, lots of extra smiles (never know when I might need one!). My wife doesn't seem to get this treatment. So I win
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