What to ask in the first month of dating
Early questions set the tone for everything after. These are the ones worth asking before you have decided who the other person is.
The first month is the only time you get to ask basic questions without it being strange. Later on, you will have built a picture of this person and stopped checking whether it is accurate. Early curiosity is cheap. Use it.
Ask what their ordinary life looks like
Dating shows you someone at their most curated. What you actually need to know is what a Tuesday looks like for them.
- What does a normal week look like for you when nothing special is happening?
- How do you recover after a hard day — people, or no people?
- What do you spend money on without thinking twice?
- Who do you talk to when something goes wrong?
Ask about the shape of what they want
You do not need a five-year plan on date three. You do need to know whether you are pointed in vaguely the same direction, and it is far kinder to find out early.
- What did you learn from your last relationship?
- What does a good weekend look like a year from now?
- Is there something you are working toward that most people do not know about?
Notice how they answer, not just what
Whether someone is curious back is more informative than any individual answer. So is whether they can say "I do not know" without discomfort, and whether they talk about the people who have hurt them with contempt or with perspective.
Early on, how someone answers tells you more than what they answer.
Keep it light. These work best spread over weeks, one at a time, in the middle of doing something else — not delivered as a list across a table.