"Sinatra-ing" My Son

I am making a list for my baby boy of rules that I want him to learn so he will be considered a modern day gentleman.  I want woman to look at him differently than the average Joe Schmoe that walks around trying to be cool. I want him to embody the inherently cool aura that surrounds some lucky few men such as Frank Sinatra. They effortlessly stroll through life with a sense of style while simultaneously having a swagger of unending confidence.
 Knowing some simple rules and using them as a guideline helps to create the core of the ‘gentleman’, but like everything, gaining experiences and creating your own style is key to becoming your own man.  So without further ado, here is my list of things that will my Matty-boy become a "Classic Gentleman".

1. Look people in their eyes when you talk to them and always shake someones hand when you first meet them.  If you aren't introduced, do not be hesitant to introduce yourself followed by a compliment when speaking to a woman.
2. When walking a lady home always have them be on the inside away from the curb on the sidewalk, or when walking in a parking lot, keep them on the side with the parked cars.  Be their protector with whatever comes and it will not go unnoticed. 
3. While at the dinner table, always stand up when a lady approaches, and if seating her, make sure to pull the chair out first and then push it in gently while she sits.  
4. Always be on time for everything, especially any appointment set with a woman.  Do not be pushy or annoyed if they are running a bit behind.  Keep in mind that they are getting ready for you, take it as the compliment that it actually is and enjoy it.  
5. Don't curse around a woman or while in public.  You really never know who is listening and making a judgement about you.  Keep it classy and keep it clean.  People that weave together a string of profanity make themselves look idiotic.  Use your mind to find better wordage and if and when you do Curse, it will bring the weight that you would imagine comes if Ward Cleaver said "F*%# You".
6. Become well read.  Being able to hold a conversation and keep it interesting starts with your knowledge about a multitude of subjects and being able to think.. Always keep learning, always keep reading. 
7. Wear clothes that fit.  Don't let your jeans or sweats hang down or wear extremely baggy clothes, but don't wear banana hammocks either.  Find your size and buy clothes that actually fit you.  You should at some point get fitted for a suit so you can confidently talk about your shirt or jacket size.  You will find that even going back to the 50's and 60's, if a man was well dressed it still comes across as someone that was and still is fashionable. 
8. Do not make fun of others.  Everyone has a time when they feel vulnerable. do not exploit that moment to try to make yourself look or feel better.  Always be the champion of others.  Also, realize what is happening around you. Being aware of your surroundings will keep you from an embarrassing situation yourself. 
9. Always be polite.  Open a door for a woman.  Give her your arm while walking.  Give up your seat to elders and women.   Help someone change a tire.  Do not interrupt someone else while they are speaking.  Do the things that people complain that "Men just don't do anymore".  
10. Be Confident. Know how to answer people when addressed for your opinion. Don't hesitate to answer when asked questions like "How do you want your steak cooked?".   Know what you like and where you stand. It's alright to have an opinion as long as it's yours.