Keeping with the theme of Valentine’s Day, there is a good chance that many couples went out for a nice, romantic dinner. You’ve had a great time together and it’s a nice break from cooking your own dinners, but then comes the most complex decision of the night. What do you tip your waiter or waitress?

I certainly can tell you some horror stories of dining out. For example, I had a waitress spill steak au jus onto my suit as they attempted to serve my food to me. Another time I had a waiter who brought the completely wrong meal out to me (it’s a pet peeve of mine when server’s try and memorize your order, ugh). Knowing how little they do make, what exactly did they deserve as a tip, if anything?

Being that I had no experience in the food service industry, I admit that I was a very stingy tipper when it came to dining out. I always felt that if they go above and beyond service, they may get the typical 15% tip from me. Since I’ve been with my wife, who has had experience as a waitress, I changed my tune a little bit.

I have read several articles over the years that I definitely have to disagree with when it comes to appropriate tipping etiquette. Many people in the ‘biz’ claim that the appropriate tip at a fine restaurant is at least 30% and should be no less than 20%, even if you had poor service. I can’t fathom tipping someone over 30% for their service unless you had a $5 meal and gave $2 tip.

Hear are some of the things that are in the back of our minds when we decipher the tip:

Was the waiter or waitress friendly? Not everyone is going to like their job day to day, but if they are having a bad day, they need to fake it. Being cheery always makes the meal go better.

Do they know the menu well? It’s important as a server to know the meals and what they consist of. Having a quick answer is always a plus, but having them peak at the menu and read the description is not the path to a proper tip.

Bringing refills is a major plus. It’s always great when a waiter or waitress is attentive enough where they bring you a refill when your drink is low. Asking is good too, but not asking if you want a refill is the worst.

Did they do something extra? I always like to ask for extra pickles with my meals (if appropriate). Typically, I won’t get charged, but when they forget the request, it always weighs on my decision. One time I asked several times, but still never got them.

How often do they stop in and check on you. Maybe I’m picky, but it’s always annoying when I didn’t even take a bite of my food and they ask how it is. Asking every 2 minutes and not letting me enjoy the meal bugs me as well.

Was what you ordered right? I would never cut a servers tip is the food is bad since it is not their fault. There have been times though that I ordered a medium well steak and get a medium rare steak. To me, I felt that the server wasn’t listening close enough. Along those lines, if you make special requests like no mushrooms, do they follow through?

Maybe giving a poor tip would send a discrete message that they need to improve their service skills and make it an incentive for them in the future. Again, it’s rare that we ever give less than 15% now, even if they have shortcomings (hey, it could be there first day!)

We have a 5.5% tax rate, so a quick method is to multiply the tax times 3 and round up if everything went smoothly! If the server was just horrendous, maybe 10%, but we’ve never stiffed a server and never plan to.

I’d like to hear your tip strategies and about your dining experiences (good or bad)!

Don’t forget to order water!

Stupidly Yours,




StupidCents was founded by Matt in 2009. His thoughts are shaped by his family and career and seasoned by his endless motivation to succeed personally, professionally, and financially.