There is no doubt that tipping can lead to some really awkward and often unintentionally insulting moments. Usually, this occurs in areas outside of waiting tables. For example, recently I had a repair man come and fix our dryer. While he was there he did some routine maintenance on our washer, for free. As he left, I tipped him and it confused him and I think it made him feel bad. He had genuinely done something nice for me because we had a good report and he didn't expect anything in return. My tip ruined all of that. I wasn't sure what the protocol was though. Why? Because everyone and their uncle expects a tip these days. If you go get ice cream, there's a tip jar, if you get coffee... a tip jar. It's everywhere these days. My thinking on this is changing the more I consider it. I would almost rather that a restaurant folded 20% in to their prices and paid the servers more, just for the ancillary effects it would have on other situations, like the "repair man".
Have I recommended Predictably Irrational yet? Ariely spends a chapter on money and friendship, and outlines how offended you would be if your in-laws tried to pay you for hosting Thanksgiving dinner. He also relates a story of the California Bar Association and their failure to get their members to give discounts to the elderly... shortly before having no difficulties at all getting their members to do pro bono work for the elderly. Even those Freakonomics twits talk about the daycare that charged a fee for late pickups to discourage them and ended up increasing late pickups. Ariely breaks this down as a mismatch between expectations - we expect one thing of paying relationships and another of friendships. He goes on to point out that most businesses, at one point or another, attempt to ingratiate themselves as friendships... while also charging you money. He finishes by pointing out that most people hate the banking industry because their only play is to try and be "a part of the family" or whatever, but your family would never charge you an ATM fee, a $40 overdraft charge, etc... so we end up hating the banks more than if they'd said "Wells Fargo - cold-hearted bastards that will keep your money safe" (anecdotal evidence of mine: Wells Fargo has the least touchy-feely ad campaign and the highest customer satisfaction) The maintenance guy wasn't expecting a tip. He was expecting you to be grateful so that the next time you needed something, you'd call him. He wanted you to owe him a favor. Instead you put a monetary value on that favor and negated it - you don't need to call him next time, you tipped him and handled it. The difference between "tips" and "bribes" is that a bribe comes first - and it will absolutely get you a good seat in a spendy restaurant or a good room at the hotel. Both are the exact opposite of a favor - in my example about the European waiter, he was giving good service because that brought you back to the restaurant which lined his pockets indirectly rather than directly (and a lot more effectively). And the fact that in the US, the culture is to give servers the expectation that: It's an untenable situation that cannot help but increase interpersonal strife. As a side note, I think it's interesting that Hubski is all about supporting the tipping culture and what a radical dick I am for saying I don't like it (while blissfully ignoring the fact that I participate in it) while Reddit is all about how stupid tipping is.
I agree with you in principle, but I suppose I'm more acquiescent than resentful. I certainly don't agree with arguments that say that waitstaff deserve tips, because they work hard. Everyone in the service industry who is good at their job works hard, and most of them don't get tips (I worked as a line cook as a teenager, and I'll be damned if I didn't sweat my ass off). It is more correct to say that waitstaff deserve tips, because they get paid slave wages otherwise, so that restaurateurs can keep (nominal) prices artificially low. I 'support' the tipping culture in the sense that I engage in it, but I don't support in in principle.
Waitstaff deserve tips because they need to make a living and we've got a bass-ackward structure in place to make that happen. It's a real "fog of war" situation right now, though - I've heard from more than a couple servers that if you really want to register your displeasure at your service, tip a dollar because lots of people don't tip on principle. Then there's the fact that there's no real agreement as to who gets tipped what and any etiquette guideline is more likely to tell you what to tip the paperboy than the data recovery specialist. Into this we've got the typical opportunities afforded by the large and organized over the small and disparate - restaurants skimming off tips, the IRS confusing the issue, etc. So what I see is a situation where everyone is pissed off - except the restaurants. I'm into pissing restaurants off.