Dating 101

Posting this blog on facebook initiated a lively discussion among my family and friends. I also got a bit (well, a lot) of heat from my former students who were visiting over the holidays.

Four questions in particular stuck out:

  • Would the rules be the same if Dillon was a girl? Would the rules be the same if Dillon was taking a boy on a date?
  • What if Dillon is taking someone on a date who does not want the door held open for them?
  • Isn’t chivalry “benevolent sexism”?
  • Shouldn’t they be guidelines instead of rules?

A1. If Dillon was my daughter and not my son, I would have a different set of rules. I think. No. I know I would. It seems that I am much more traditional than I thought I was.  However, I think it would incredibly valuable if others shared their dating rules for their kids with me. For example, I wrote these for Dillon who is 13 and without a phone. How would the rules change is Dillon was 16 and driving? What if Dillon was a girl? What if Dillon was gay? It would be great if you all took the rules below, edited them for your child’s context, and shared them in the comments section below. I’ll turn them into a pdf (maintaining your authorship) and include them in the post. I think it would be valuable to begin a library of dating rules. 

A2. When Kyra and I started dating in college, I vividly remember trying to pay for her dinner on our first outing (it was a group dinner with her friends). She vehemently stated “I do not need you pay for my dinner.” She also did not take kindly to me opening doors for her. Over time, we had multiple conversations and had to find common ground upon which we could both exercise our values.

A3. I found this article regarding chivalry and sexism enlightening: “Chivalry Isn’t What You Think It is! A Woman Explains.” I want to thank my friend Chris Kilmartin for bringing this issue to the fore.

A4. Yes.

 So, after talking this all over with Kyra, here are the steps we have decided to take with Dillon and the discussion of dating.

  1. We will review the rules as a family and have a discussion regarding our own experience navigating these rules when we first started dating. We will also talk about chivalry (using the reading above as a source). 
  2. We will reiterate that rules below are his starting point. 
  3. We will let him know that he and his date can have their own conversations about these rules. Here’s an icebreaker my friend Chris Kilmartin proposed. Dillon could ask: “What did your parents tell you about how you’re supposed to behave tonight? My dad made a list so long I can’t even remember some of it.”

Here are the Rules Guidelines:


Plan out your date. 

  • What will you be doing? 
  • Where?
  • When does the date start? 
  • When does it end? 

Share this information with your date so that your date can share it with their parents.

Visualize the date from beginning to end so that you will be mentally prepared for what to do and when to do it.

Make a list of interesting questions to ask your date. 

Clean yourself up. Take a shower. Put on deodorant.

Dress nice.


If you are meeting up in a common area, be the first one there and stand up and greet your date upon their arrival.

You open all doors.

You buy all food, drink and tickets and cover all entry fees.

If you are eating at a restaurant or a food court, then you follow your date to the table. However, if it is very crowded then you lead and make the way to the table.

Pull out your date’s chair.

Your date sits down first.

Your date orders first.

At the table, place your napkin in your lap.

Do not start eating until your date’s food has arrived. Don’t eat too fast. Don’t eat too loud. Keep your mouth closed.

Don’t gulp your drink, sip it.

No belching. And, if you cannot help it, say “Excuse me.”

If you need your date to pass you an item on the table, don’t reach and grab. Ask “Can you pass me the ___?”

No swearing.

No bragging.

No talking poorly about others.

When your date is talking, look them in the eyes and listen. 

Ask your date interesting questions (see above).

Be kind and courteous to others around you and your date.

When walking in public, you walk between your date and the street and/or parking lot.

When crossing the street or parking lot, keep your head on a swivel and before crossing make sure that it is safe for you both.


Tell your date “Thank you for a nice night.”


Follow up the next day and tell your date “I had a nice time.” 



If you enjoyed this blog, you may enjoy my This is the Work newsletter.

Thanks. – shawn