The Journal
What to actually ask in your first matchmaking conversation
May 5, 2026 · 5 min read
Skip the small talk. Here are the questions Auntie wishes every brother and sister asked in their first call, and the ones to avoid.
First conversations on dating apps are mostly performance. First conversations through Auntie don't have to be.
Ask things that test temperament
- · Tell me about a recent conflict and how you handled it.
- · What did your parents' marriage teach you to copy, and to refuse?
- · When you're stressed, what do you reach for?
- · When was the last time you changed your mind about something important?
- · What's something your closest friend would tell me about you that you wouldn't?
Skip these
- · Favorite colors, foods, movies. Trivia is not data.
- · Long lists of preferences and dealbreakers. You'll cover those with Auntie.
- · Career questions you could Google.