When did I make you proudest?

Why this question works

Most parents are prouder of their children than they ever manage to say. Life is busy, and praise gets saved for report cards and ceremonies. This question gives your mom or dad a direct invitation to say it out loud, and gives you the chance to hear it in their words.

The answer is nearly always a surprise. Parents tend to be proudest of character: the time you stood up for someone, kept going at something hard, told the truth when it cost you, or were kind when you thought nobody was looking. Hearing which moment they chose shows you what they value and how closely they were paying attention all along. It is a good conversation at any age, and a wonderful one to have as an adult, when you and your parent can talk as two grown people who know each other well.

How to ask it

This can feel like a bold question to ask, so set it up kindly. You might say you have been thinking about the family story and realized you have never asked. Choose a private, unhurried moment: a long phone call, a walk, an evening when the house is quiet.

Ask sincerely and then simply receive the answer. Resist the urge to brush it off or make a joke. Say thank you. Then turn it around and tell your parent when they made you proud, because they have probably never heard that either. If your relationship has had difficult seasons, this question can be a gentle way to remind you both of what has always been good.

Other ways to word it

• Is there a moment when you were especially proud of me?
• What is something I did that made you think, that is my kid?
• When did you first see the adult I was going to be?
• What have I done that you still tell other people about?

Follow-up ideas

• How old was I?
• What exactly did you see me do?
• Did you tell me at the time?
• Was it something I found easy, or something I had to work at?
• What did it show you about me?
• Did it remind you of anyone in the family?
• What are you proud of in me right now?

An example answer

This is an invented example, written to show the kind of detail to listen for. Your dad’s answer will be his own.

"You will think I am going to say graduation. I was proud that day, but that is not the one. You were eleven, and you were playing in a baseball game, and the other team's pitcher was having a terrible afternoon. He walked four batters in a row and he started to cry on the mound. Some kids were laughing."

"You were on first base. You called time, walked over to him and said something. I never did find out what. He wiped his face and nodded, and you jogged back to first as if nothing had happened. Your team lost that game. I sat in the bleachers thinking that I did not teach you that; you just knew to do it. I have thought about that walk to the mound more times than I can count. That is the kind of person I hoped you would be, and you already were."

What to write down

Write the moment down as your parent told it: how old you were, where it happened and exactly what they saw. Record what they say it showed them about you. Then add the moment when they made you proud, and tell them what it was. Date the page. It is one you will be glad to open again whenever you need a lift.

The Tell Me Your Story journals for Dad and Mom ask a question like this one in the chapter about raising you, on a page of its own. Some things are easier for a parent to write than to say, and a handwritten answer to this one is a page you will keep.

See the Tell Me Your Story, Dad journal or the Tell Me Your Story, Mom journal. For more ideas, read questions to ask your parents or browse family and parenting questions.