From The Blog

Fathers letter to Son on First Date

Fathers letter to Son on First Date

In late October, in a Man-Making Blog post titled: Advice for A Young Man’s First Date, our good buddy in the USA, Earl Hipp, quoted an article we posted on our Facebook page. Earl is the author of Man-Making and has worked with men and boys for over 30 years. The article was written by a mother to her son and titled, 10 Things a Boy Must Know Before His First Date.

This got me thinking a bit deeper about advice to young males. I liked the letter by the mother but wondered if young fellas today would read it and get it, so I replied to Earl, . . . it has some really lovely points, but it is written by a woman, and some boys will pay it zero heed. Perhaps a man’s voice to compliment the list and say similar things in a different way would help boys understand or ‘get it’.

So Earl lovingly returned serve and asked me if I’d take a whack at a blog describing a list a man might offer his son, or any young man on the occasion of a first date. Here’s my whack!


I’m proud to see that you’ve grown and matured into the fine young man that you are today. On this happy occasion of your first outing with a young woman, I’d like to offer a few suggestions. It has been said, and I agree, that one true measure of a man is how he treats women. I know that you are a good person.

“Son, I’m proud to see that you’ve grown and matured into the fine young man that you are today.”

However, there are some pitfalls along the way to learning how to treat women where even good men can find themselves in difficult places they could not have imagined. So here, in no particular order, are a few suggestions. They reflect my own learning and growth, and some, or a lot of it comes from getting it wrong myself!

1.     Look her in the eyes, don’t stare, but when she is talking to you look her in the eyes. It’s not natural for most blokes but it matters to most females. If you find this difficult to hold for too long, try looking into one eye at a time or at the tip of her nose, or her mouth.

2.     Get to know her as a flesh and blood person. Less flesh and more blood really. Who is she? What does she like? What matters to her? What are her experiences of life? What are her hopes for her future and dreams for the next week, year, or the next decade? Look for common ground in areas like her music, interests, friends, experiences. Showing interest in her will make her feel special and valued, and you may just find you have things in common.

3.     Breathe! It can be easy to feel swept away in her company. Treat her with respect and if you catch yourself feeling overwhelmed, remember she is human like you. Imagine you are talking to someone’s daughter, sister, or a friend. In truth, she is someone with needs, challenges, and gifts like you and the rest of us.

4.     Compliment her and value her opinions. Inquire deeper when she shares something of herself. This is not prying but being interested in her and what makes her tick.

5.     She is not impressed by you talking about yourself all the time. When boys talk, it’s often about conquest and achievements. Big noting (bragging) shows insecurity and a need for a ‘me focus.’ Be interested in her and who she is. Let her do most of the talking… breathe, relax, and be yourself. If she asks, speak more about what you love and enjoy doing (your own dreams for the future), she may find that more interesting than your accomplishments.

6.     Take a risk to be vulnerable and humble. Tell her about some things that might be a little hard for you to talk about, like a current challenge in your life, a time you made a mistake or when you were embarrassed.

7.     Laugh at yourself; don’t be too important and serious. If you are drawn to each other for a second or third date, you need to be comfortable with each other. Don’t pretend to be someone you’re not by putting up an image you think she will like. Personal honesty always comes across the best.

8.     If it’s not meant to be, if you’re not a good match, be grateful for the opportunity to have spent time with her. It might hurt a little to get some rejection. Think of this as practice that will help you to be better prepared when you meet a young woman who’s a better match for you. Females talk with each other about these things and she may well have a friend she wants you to meet. If that were to happen, what would you want her to say to her friends about you?

9.     Be true to your word. Showing up on time is honorable and when all else fails, a man’s honor is what will carry him through. If your first words are ‘sorry I’m late,’ it’s not a good start and says something about you.

10.   You have a flood of testosterone flowing through you. If your main thoughts about her are about having sex, use your other brain! Sex for the sake of sex can leave you feeling empty and unfulfilled. She is not a trophy you can talk to your mates about. I promise you the memory of your first sexual experience will be with you all your life. Make it an experience you will feel proud of and with someone you care about as a human being. This means making sure the timing is right for you both.

If she instigates sexual contact be very careful. This might say something about her insecurities and one hot moment could change both your lives forever. Some women have confused sex for love and give sex as a way to get love. I’d say, just enjoy her company this time and get to know her first. If you find out you like her as a person, I’ll be very happy for you and you’ll have had a really great first date.

This list could be much longer and I don’t consider it to be ‘the complete guide’. These words are what has come to me when I think of what I would have liked to know at your age. I do know the young man you are, and I know you will do your best and probably the right things. Mostly, I want you to know I love you, I’m excited for you, and proud of you. Have fun, and if you’re willing, come tell me how it went. It’s important to me that know I’m here for you whenever you might need me.

Love, Dad

As a father of 2 daughters (20 and 8), and 4 sons (17, 15, 13, 11) this is a timely exercise. When I reflect on my young adulthood, a letter like this (despite it’s discomfort) from my dad or older male would have been quietly well received.

So this begs some questions for you;

  • Did anyone give you any advice prior to your first date?
  • If you can still remember, how did your first date go?
  • What would you add to or change on this list if you were called to support your son or other young man going on a first real date?
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