On a first date you’re trying to learn how someone spends their days and what they care about, without it feeling like an interview. The questions below come in three groups. Start with the easy ones about evenings, food and places, move to stories and interests once you’re both comfortable, and keep the last group for when the conversation is going well.
Keep it a conversation
Ask one question at a time and answer it yourself as well. When an answer interests you, stay with it: “How did you get into that?” usually leads further than a new question. If a topic stalls, go back to something concrete like food, travel or the neighborhood.
Questions that invite a story tend to tell you more than questions that ask for an opinion. A story shows you someone’s humor and how they talk about other people.
What to avoid on a first date
- Detailed questions about past relationships
- Several questions in a row without sharing anything yourself
- Questions that sound like you’re checking them against a list
Before and after
Meet somewhere public and make your own way there and back. If it goes well, second date questions build on what you learned. For a blind date set up by a friend, blind date questions start with the setup itself, and questions to get to know someone work outside dating too.
The 36 questions to fall in love are a longer, structured exercise that suits a later date better than a first one.