The Twentysomething Whisperer

The Twentysomething Whisperer

Redefining the Relationship: Part II

29 Questions to Ask Your Twentysomething

Meg Jay's avatar
Meg Jay
Feb 17, 2026
∙ Paid

Redefining your relationship with your twentysomething is about making it a connection between two adults. Although you probably know a lot about the kid who used to live in your house, you’ll need to spend some time being curious about who your twentysomething is (so far). Show them you’re interested in what they’re up to and what they think.

Here are 29 conversation starters for drives, hikes, dog walks, dinners, leaf raking, coffee, or downtime. Don’t try to ask all or many of these questions at once. Your twentysomething can always feel free to pass. Although some of the questions are about family, let your twentysomething see you’re mostly interested in them.

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