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The Shifty Traveler: The Lost Art of Tipping Well

leaving a big tip

I travel for a living (yes, I have a day job) and am a ‘regular’ at many bars, restaurants, hotels and diners.  Where I go, people remember me.  Why?  Not only am I charming and naturally memorable, but I also tip well.

Unless you live under a rock or never earned your Man Card, you’ve seen Reservoir Dogs.  Do you remember the tip scene from that movie, where Mr. Pink doesn’t believe in tips?  The rest of the group gives him shit, and deservedly so.  However, there is a more important reason for a man to tip, and to tip well:

Servers, Valets, Bartenders… they will remember you if you’re a shitty tipper.  But they will also remember you if you’re a big tipper.

leaving a big tipNow I’m not saying to tip $1,000 on a ten-dollar tab.   If you do, that’s your business (and you’re probably trying to get laid).  For me, I go by a simple rule in restaurants:  $5 or 20%, whichever is more.

What this does for me is get me remembered.  If I tip big at a bar in October and come back in November, December, etc. they’re going to remember me, remember I’m a good tipper and go the extra mile for me.  Bartenders pour a little extra.  Valets run instead of jog.  For a small period of time, I’m pampered.

And what does it cost me?  Virtually nothing.  The difference between a $10 and $15 tip is minimal to me, but memorable for someone making minimum wage (or less).

If you’re willing to give a little extra at your regular hangouts (and want to reap the rewards) use this handy guideline:

  • just the tip tip jarCoffee shop, leave $1 for a coffee or quick drink, $2 if it’s a specialty drink or latte.  If you’re ordering a soy-milk half-caff upside-down caramel macchiato, recognize you’re making them do extra work and tip accordingly (and why the fuck are you ordering such a namby pamby drink??).  If picking up coffee for a group, tip 20% of the tab.  I do this and get bumped up to the front of the ‘drink order’ line when they’re busy.  Gets me in and out quickly, gets them cashola.
  • Valet service, $5 tip when handing over your car (so they realize you aren’t a cheapskate) then another $5 when they bring your car back.  Ten bucks will typically double their hourly wage, and will virtually guarantee they’ll be nice to your ride.
  • Bartender.  $1 per drink, minimum.  Even if you’re running a tab, leave a Washington at the bar every time you get service from them.  Then, if you want to add a little icing to that cake, leave another 5-10% at the end of the night (with a little note “Thanks, I’ll be back.”).  If you have someone serving you the drinks (cocktail waitress, bottle service, etc) make sure to tip them AND the bar.  The bartender pours you the alcohol, so keep them happy and a 1oz shot will miraculously grow.

You can also tip housekeeping at hotels, mailmen, etc.  Whenever you want ‘above and beyond’ service from someone you deal with on a regular basis, tip them and tip well.

(And here’s a tip from me, in a digital age.  If you’ve worked in the service industry, you know tips get taxed if you add a tip to a credit card swipe.  Been there, done that.  This is why I carry cash around at all times, mostly in 5’s and 1’s.  I usually have a money clip in a front pocket, with five 5’s and ten 1’s specifically for tipping.  This makes it easy and quick for me, and tax-free for them. )

Do you tip?  What rules do you follow while tipping?  And if you’re in the service industry, please chime in as well.  Show the world why tipping is important, and a little mutual back-scratching can go a long way.

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