It was a little interesting this week watching my youngest child-20-year-old son-navigate through solving a problem alone.  He hasn’t talked to me yet about his problem. Now, in almost every situation, where I noticed there was a mood-altering problem, he has come to me and we talked through his problem. Usually at this time, the conversation is about the problem, how he handled it and him asking me if I think he handled it in a good way. I hope this time won’t be any different.

Now, I have had special moments with each of my children, certainly more than once. These moments often remind me of the special moments I had with my mother.

As a daughter of a single woman who parented alone, my mother made a big deal about our special moments. She would take me to a very nice and elegant restaurant. (My favorite was The Fish Market in Philadelphia where I believe the restaurant sat on the second or third floor) We would dress for an evening out, and I would get excited to order a Shirley Temple. It was during these special moments, she shared things like navigating girl friendships and how I should expect to be treated while on a date. It was this setting where she talked to me for the first time about the joys of experiencing being a woman every month and the responsibilities that came with it.  (now that I think about it, that glamorous conversation was exaggerated). It is these moments that I have carried out with my children.

These moments come often while raising children, and at any age I think it’s important to make them memorable. I have many of these same kinds of memories with my children. Often times they did not occur in an elegant restaurant over Shirley Temples-mainly because I had three children not one-but they have been memorable just the same. I think it’s time to plan another with the baby boy.

A man loves his sweetheart the most, his wife the best, but his mother the longest. ~Irish Proverb

Prior to realizing it was time to share some one-on-one time with my youngest son. I noticed a post my friend wrote on Facebook the other day. In that post she too mentioned a random conversation she had with her soon-to-be 18-year son, also her baby.  She captured a lot of what I shared with my son previously and some I hadn’t. But they were written in quirky and nice catchy phrases that I thought would go nicely in this upcoming conversation with my son.

But then in that quick moment, as I prepared for this special conversation, I realized I had added more catchy and quirky items which resulted in 50 items.

As a result, here are our-my friend’s and my-50 Rules for my son….

  1. Never do anything that would cause you to lose your driver’s license, your right to vote, your passport or your integrity.
  2. Always own a tux, you never know when you will need it.
  3. Save 20% of your income. Emergencies happen and they need to be handled.
  4. Always plan the first 3 dates when you go on a date.
  5. Have one meal you can cook that would impress anyone.
  6. Never bring up sex at first. It should always be her idea and on her terms.
  7. Never get drunk. Know how to hold your liquor.
  8. Always go to work and never be late even when you own the company. People are depending on you.
  9. Always sit facing the door. You need to know what is going on.
  10. Never stop learning. Knowledge is power.
  11. Never brag about how much money you have, the things you own or the women you have slept with. It shows no class. People need to know that you have been there before and that you know what to do.
  12. Never live anywhere that does not have your name on it. The mortgage and deed, the lease.
  13. Never shake a man’s hand sitting down.
  14. There are plenty of ways to enter a pool. The stairs aren’t one.
  15. The man at the grill is the closest thing we have to a king.
  16. In a negotiation, never make the first offer.
  17. Act like you’ve been there before. Especially in the end zone.
  18. Request the late check-out.
  19. When entrusted with a secret, keep it.
  20. Hold your heroes to a higher standard.
  21. Return a borrowed car with a full tank of gas.
  22. Don’t fill up on bread.
  23. When shaking hands, grip firmly and look them in the eye.
  24. Don’t let a wishbone grow where a backbone should be.
  25. If you need music on the beach, you’re missing the point.
  26. Carry two handkerchiefs. The one in your back pocket is for you. The one in your breast pocket is for her.
  27. You marry the girl, you marry her whole family.
  28. Be like a duck. Remain calm on the surface and paddle like crazy underneath.
  29. Experience the serenity of traveling alone.
  30. Never be afraid to ask out the best-looking girl in the room.
  31. Never turn down a breath mint.
  32. In a game of HORSE, sometimes a simple free throw will get ’em.
  33. A sport coat is worth 1000 words.
  34. Try writing your own eulogy. Never stop revising.
  35. Thank a veteran. And then make it up to him.
  36. If you want to know what makes you unique, sit for a caricature.
  37. Eat lunch with someone new, often.
  38. After writing an angry email, read it carefully. Then delete it.
  39. Ask your mom to play. She won’t let you win.
  40. See it on the big screen.
  41. Give credit. Take the blame.
  42. Write down your dreams.
  43. When you give your word, keep it.
  44. Never loan money you can’t afford to lose.
  45. Don’t let anyone mess up your money. Therefore, it is a good idea not to date anyone you work with.
  46. Never let anyone know when you do not have any money.
  47. Get in the habit of taking your lunch to work or school it sharpens your planning skills and saves money.
  48. Never spend until you have no money.
  49. Never be afraid to end a relationship, work or personal, but do it tactfully.
  50. Some of your closest friends should be women.

As I write these, I cannot help by laugh. As a mother of two young men (and also a young lady), I was a different mother when my eldest was 20 (who is now 29). I shared a lot of do’s and don’ts with him but not the way I will share them with the youngest. Even as I wrote this list, I thought, I will share this list with my oldest. However, this list of quirky and catchy phrases won’t work with him. He is a deep and contemplating young man although he has a fun humor just like his mother. My special moments are more like conversations around our experiences, how they differ, and who we are as a result of them. While he knows a lot of these rules already, I will probably learn something new from him as a result of our special conversation.

In the meantime, I look forward to this special moment with the baby boy and I can only hope that this helps him move past this troubling time he is experiencing now as well as in the future.

These rules were written as a collaboration with my friend, Dawn Richardson.