10 People I Don't Know How to Tip

I consider myself a reasonably good tipper. Both Lori and I have worked for tips in the past (Lori was a waitress and me...well let's just say the G-String doesn't fit as well anymore) so we feel a little pull to make sure we're at an appropriate level with our gratuities. A lot of it is pretty basic. Restaurant waitress - 20%. Taxi driver - 15-20% (unless it's the San Francisco Taxi driver...he's different). Pizza guy - usually around $5. These are the easy ones, but there's a whole group of other people that I always fumble with. It feels like I should be tipping these people so I try and do it by feel, but I'm drastically inconsistent sometimes and I'd really love to have a set plan in place. These are the ten people who I don't seem to have a solid handle on tipping:

#1 - The Front Desk Agent
We're not talking about the $20 trick in Vegas here. I also don't mean your standard check-in experience which takes all of 30 seconds and has no frills. My hesitation comes when the word "upgrade" gets thrown out there. I honestly don't know if I've been blocked into a better room or if the front desk agent has merely noticed an opportunity to get me into something nicer. If it's the agent doing the work, I'd kind of like to offer a token of appreciation, but it feels a little awkward at the front desk. Of course it would probably feel a little more awkward if I came around behind the counter and tried to slip some money into their pocket, but that's another story altogether.

#2 - The Bellhop

OK, I know the rules for this (although the bellhop at the Plaza might disagree), but I get confused when they split it up. One guy gets your bags out of your car and puts them on a trolley, then another guy brings them up to your room for you. Is it supposed to be $1-$2 per bag each? I've read that I'm supposed to tip the guy who brings them up to the room, but I feel like such a cheapskate not giving the guy who empties my car anything. Especially if it's our own van. Those rental vans are clean, but anybody willing to unpack the back of our personal van, deserves a few bucks.

#3 - Taxi Hailer
Seriously...no idea. I think I'm supposed to give a buck or two, but I very rarely do. The exception is the guy at Caesars Palace, who has this whole dance move/yoga pose/tribal chant thing that he does to call up the next cab. I'd give him a couple bucks, even if I didn't need a cab.

#4 - Car Rental Lot Guy
OK, this one might fall more under bribe than tip, but I've noticed that if you rent a midsized car and ask for directions from the lot guy, he'll point you to the midsized row. If you ask for directions with $10 in your hand, he quite often points you to an entirely different row. This only seems to work in certain places (Vegas, surprise!) so I'm never sure where it's commonplace or if the lot guy is going to look at me blankly. Lori loves to laugh at me when I try something like this and it fails miserably. Maybe I'll just claim that I do it for her entertainment.

#5 - Housekeeping

There's a bag of these somewhere...

I've settled on how much to tip housekeeping at $2-$3 per day, a little higher if we have a suite. We also only take housekeeping every other day, so we're normally leaving $5 or $10 for the room attendant (Is that the proper term? I'm avoiding the word "maid" here.) whenever we have our room cleaned. My problem comes with how to tip them. I usually leave it on the desk with a note saying "For Housekeeping", but I've heard stories of the housekeeping supervisors coming around ahead of the room attendants and collecting all the tips. There's also the people who do the nightly turn-down service. We almost always refuse turn-down service...unless they have chocolate. We never turn chocolate down , but what's the appropriate tip for somebody who brings chocolate directly to your room? My kids say $100 if she leaves the bag, but I'm looking for a slightly more affordable option.

#6 - Door Holder Guy
That's probably not the technical term for his job (Doorman?), but he's always there opening the door for everybody as they come in and out of the hotel. He's another guy I kind of feel like I should give something, but I very rarely do since I'd go broke pretty quickly considering how often I go through those doors. I think I might have seen people tipping the door guy in movies or something, and that's why I feel like I should be tipping. Sometimes I try to find a side door or a back alley that I can sneak in through, just so I don't have to worry about it.

#7 - Concierge
Just the name scares me, and I kind of feel like I should be able to speak fluent French just to talk to the guy. I know to tip him if I ask him to arrange something for me like show tickets or flowers in the room (I can hear Lori laughing now), but when I just want directions to something, it seems like overkill to be tipping big bucks. He also doesn't seem like the kind of guy you can give a dollar or two. The name implies high class, and that seems like a $20 minimum to me.

#8 - Valet
I love places with free Valet Parking. There it's easy...a few bucks on the way in, and a few bucks on the way out. Where I have a problem is at hotels who are already dinging me $45 a night for valet parking. There I choke a little at handing over more money to the guy taking my car, but it's not his fault that the hotel charges so much. Of course some places just make me nervous handing the keys over at all. I know it's just the flooring they use in the garage, but the valet lot at the MGM Grand in Vegas constantly sounds like there's a Fast and the Furious drifting race being shot in there.

#9 - Room Service
Hotels seem to have taken it upon themselves to solve this one for me by pre-adding an 18% gratuity to the bill. I can live with this, but it's the line underneath labelled "additional gratuity" that annoys me. On a blank check, I normally would just tip 20%, but if I add the 2% difference to the additional gratuity line, I can end up writing in things like 73 cents. Doesn't that make me look cool?  I feel like a bit of a dork leaving the line blank, but it's probably better than adding quarters to the total.

#10 - Shuttle Driver

If this is your shuttle, I'd tip your driver.

I'm all over the map with this one. Sometimes I don't tip, sometimes it's a couple bucks, sometimes it's more. I really don't have a reason for it either, other than perhaps they made me smile or laugh with their banter. Of course some days I'm just tired and cranky, and they'll get a better tip if they keep things quiet. It's really kind of cheap of me considering there's five of us, so throwing a buck in the drivers basket only works out to twenty cents each. There's really not too much else I can do with the dollar anyways, other than put it towards the $100 bag of chocolate that housekeeping is hiding from us.