ingridsf, on Apr 12 2006, 04:28 PM, said:
A cautionary note: I was with a nice guy once who also thought a little strategic pre-tipping was the way to go. We were in a swell-elegant type steak joint. Bottom line, not everyone should attempt this maneuver. Particularly if you feel at all hesitant about it. It was extremely awkward. I so wanted to give this "tip" to him: You're less likely to be embarrassed by flashing good manners than cash.
Here's a question: Have any women tried this practice?
Heh. I tried it, once, but you see, I had an excuse. I was shepherding my parents through a 25th wedding anniversary day in New York City--a Broadway matinee followed by a nice early dinner at the Russian Tea Room. This was when I was of an age (twenty-something) when this kind of day was completely terra incognita to me, so I was nervous to start with. Worse, instead of my parents enjoying being treated like this, they were paradoxically getting as whiny as 3 year olds as the day progressed. I think they just couldn't handle their eldest daughter being in control, and spending money on them; so like nice mature adults they dealt with it by acting out

(example, my dad stubbornly insisted on circling the block ad nauseum for a street parking space--in midtown Manhattan yet--ignoring all my pleas to let me pay for a goddamn parking garage; and at some other point he and my mom got in this pissy fight with each other right there in the car).
So by the time we got to the restaurant, I was a bit of a nervous wreck. I had a reservation (which I had obsessively checked and rechecked), but now I was terrified the maitre'd would take one look at this lumpen suburban family doing the Lockhorns thing and seat us near the kitchen or some damn thing, which would have inevitably provoked another parental meltdown. So, all afeared and trembling and not suave in the least, I attempted to press a twenty on the maitre d'. Very fortunately, he must have totally grokked the situation in an instant--bitchy parents, sweating-nervous daughter, other offspring already lookign exasperated--and waved off my twenty with a little laugh. We got a perfectly fine table, and while they didn't fawn over us, we did have perfectly nice service.
I have never had occasion to try such a maneuver ever again, but I do have some sympathy for the kind of social emergency for which offering such a tip can relieve a helluva lotta stress.
Oh wait--I have also tried, in a couple of other desperate circumstances, to bribe hotel catering staff to bring a couple cases of bottled water for the very parched band I was then working for (you would not believe how many times it happened that the event planner for whatever gala we were playing failed to make our promised water materialize, even after numerous requests and references to the explicit requirements in our contract rider, I might add--yeah, band riders are sometimes a source of great amusement for some, but you would not believe the amount of water needed by a hard-working band playing for four hours straight). So yeah, when this kind of crap would happen, I was empowered by the bandleader to blow some petty cash on getting them some water so they didn't blow their singing voices out. Sometimes it worked, sometimes not.