It's official.

My wife and I recently became the meanest parents ever to walk the face of Westport. We "forced" our 9-year-old to attend an etiquette class. It reminded me of the typing class my mother forced me into years ago. It was probably the worst grade I had gotten during that time and it wasn't until email became a daily event that I now thank her for caring enough to ruin my GPA.

I started to think about what "money etiquette" I should be teaching the kids and what came to mind is "picking up the tab." I learned this from my father who, to this day, is very quick to attempt to pick up the check in most social situations. That's not to say he doesn't let others pay, but he is never shy about reaching across the table to try to pick it up.

What lesson was he trying to teach me? Well, I can think of a few such as:

Be generous

Don't be entitled

Spend money on things that are important, presumably taking time to break bread with friends is a worthy value that I'm starting to appreciate more and more as I get older.

Since this habit was ingrained in me, I've now become mindful of people who don't ever try to pick up the tab, and I don't just mean at lunch or dinner. I understand that they may not have the financial capacity to pay.

But it certainly would be nice for them to at least attempt to pay. I could have used the word "pretend" in place of "attempt" there.

Offering to pay is a sign of respect for another. It's a sign of gratitude for the relationship.

I'm not suggesting that a relationship should be one of keeping score: I pay now and you pay next. For example, I can tell you I have never let one of my employees ever pick up the tab at lunch. Never.

But I do remember those who offered to pay. Those people are so few and far between that I'm impressed when it happens.

I recently pulled the "give my credit card to the waiter when my friend isn't looking" move while I was out to dinner with one of my mentors. He is ridiculously wealthy and almost seemed angry at me that I would pull a stunt like that.

The conversation ended with me saying, "Look, I've known you for years and when I was younger you picked up the tab for everything -- all the time, when I had no financial capacity to do so. Now I've got my feet on the ground financially and it's my turn to give back and say thank you. I can't help that everyone in your world just assumes it's okay to take-take-take but I don't roll like that. Get over it and enjoy the respect."

He was still ticked, but as he flew his private jet home I'm sure he smiled and knew that he did a good job having that influence on me.

And one day your kids will feel the same about these lessons you're teaching them.

Tom Henske is a Westport resident and partner with Lenox Advisors, a wealth management firm with offices in New York and Stamford. His "Money-Smart Kids" appears every other Wednesday. He can be reached at