What was your first date like?

Why this question works

First dates are remembered for their small disasters and small triumphs, which makes them a joy to hear. The picture show that neither of them watched, the milkshake with two straws, the father waiting on the porch at ten sharp: these are the scenes that make grandchildren see their grandparents as young people with butterflies in their stomachs.

The question is also a wonderful window into how courting used to work. What was a date, exactly? Where could a young couple go, how did they get there, who had to give permission and what time did the evening end? The answers are often very different from today and they lead to lively conversations across the generations. Underneath the details, though, the feelings are the same ones your own teenagers know, and that is a nice thing for everybody at the table to discover.

How to ask it

Ask it when the mood is cheerful: over dessert, at an anniversary dinner, or when a grandchild announces a first date of their own. If both grandparents are present, ask each for their own account and let them tease each other about the differences.

Keep it playful and specific. Ask what they wore, what they ordered and whether there was a goodnight kiss, and accept a twinkle in place of an answer to that last one. If your grandparent is telling it alone, give them time to enjoy it. This is usually one of the happiest memories a person has, and they will often tell it with a laugh.

Other ways to word it

• Where did you two go on your very first date?
• How did the first date come about? Who asked whom?
• Were you nervous before your first date?
• Did the evening go the way you planned?

Follow-up ideas

• How did you get there, and who drove?
• What did you wear?
• What did you talk about?
• How much did the evening cost?
• What time did you have to be home, and who was waiting up?
• What did you think when you said goodnight?
• How long before the second date?

An example answer

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

"I took her to the county fair. I had four dollars, which I thought was a fortune, and I had borrowed my father's truck on the condition that I wash it first. I washed it twice. I wore my one good shirt and enough hair tonic to stop a clock."

"I spent a dollar and a half trying to win her a stuffed bear at the ring toss and did not come close. She finally took a turn and won it on her second throw, and then she handed it to me. We rode the Ferris wheel, and it stopped with us at the very top, and I was so nervous I talked about the price of corn the entire time. She says that is when she decided I was worth a second date, because any boy that nervous must be sincere. I still have the bear."

What to write down

Note the date or the season, the place they went and how they got there. Write down what each of them wore, what the evening cost and who paid. Record the moment that nearly went wrong and how it turned out, and what time your grandparent had to be home. If both grandparents tell the story, keep both versions, with a note on who said what.

A question like this one follows the meeting story in the love chapter of the Tell Me Your Story journals for grandparents. Each has a full page, so the fair, the borrowed truck and the stuffed bear are all written down for the family to keep.

See the Tell Me Your Story, Grandpa journal or the Tell Me Your Story, Grandma journal. For more ideas, read questions to ask your grandparents or browse love and marriage questions.