Minion of Joss
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Several years working miserably in food service while I tried to be an actor taught me some serious rules for when I myself dine out.
1. Tip generously: your server is almost surely underpaid and overworked. A good general principle is 20% for good service, 15% for mediocre service, and only tip below 15% if your service really, really-- and I mean really-- sucked for no reason. A server would pretty much have to give me the finger right in my face or badmouth my religion for me to stiff them altogether. If I am a regular someplace, and know and have a good relationship with the server, I may tip over 20%. (Also, when I was single and sometimes tried to pick up cute waitresses, I would tip over 20% the first couple of times I dined there to try and get associated with a pleasant experience: worked maybe 50% of the time....) I also never tip less than $5, unless my bill was less than $5, or unless the order was extremely minimal (e.g., a 'sit-down' coffeehouse, where a large beverage and pastry may come out to be more than $5, but one is intended to sit for a long time, and it is not really a venue for "meal" type food).
2. Take time into account. If you just got in before closing, tip a little better, because you're prolonging their day. If it's busy and you've been sitting there shmoozing and drinking tea for two hours, tip very well, because you may have cost them several customers. If it's dead and you've been sitting there shmoozing, you could get away with not tipping extra on the basis that you haven't cost them customers, but it would be nice of you to tip a little extra given that you're all they have. Likewise, if you're dining on a national holiday, when one might conceivably want to be enjoying vacation, tip extra: chances are they didn't want to be there, and they can't afford not to be. Yes, salaries are time and a half on national holidays, but believe me, that in no way makes it worthwhile. Nobody wants to work on holidays who can afford not to.
3. More = more. If your orders were complex, you made changes, you asked for something off-menu, you were part of a large party, or you ordered a zillion things...tip extra.
4. Trouble = $. If you brought a crying baby, a tantrumy toddler, an ill-mannered senior citizen, tip extra. Likewise, if your date was a bitch to the server, tip extra. If your skeezy friend hit on the server in the most pathetic and disgusting way, tip extra. If you belatedly realize that you snapped at the server for no reason, or otherwise were an a-hole, tip extra.
5. Crappy swag does not equal money. Do not attempt to substitute for lack of a tip by giving your lucky key ring, that cool lighter you won at skee-ball, the foul ball you just caught at the game, the fuzzy dice from your car, your hilarious wind-up dancing penis toy, or other such items. That's just making it worse. Awesome swag can equal money: the iPod from your Awards Gala goodie bag is definitely acceptable as a substitute for your $25 tip. Other kinds of swag depend greatly on the situation. When I delivered pizza for a living, college students who had scraped together enough couch money for a pie, but not for a tip, would sometimes tip me with a little nug of weed: that will work. More borderline, but also acceptable: the guy who should've tipped me $20, but instead tipped me $5 plus a Romeo y Julieta Cuban cigar. For the most part, though, just tip: don't try the substitution. BTW, sexual favors are not an acceptable substitution unless you are extremely hot (hotness must be by acclaim, not by self-approval).
6. If you don't have a lot of money, and can't tip very well, tip as best you can, and make up for it by being as nice as possible: calm, understanding, pleasant, and friendly are often in short supply from customers, and their appearance in you-- plus, perhaps, a genuine word of thanks-- can really help make up for a more meager tip.
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Dull sublunary lovers love,
Whose soul is sense, cannot admit
Absence, because it doth remove
That thing which elemented it.
(From "A Valediction: Forbidding Mourning" by John Donne)
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