Questions to ask your boyfriend or girlfriend

If we had to plan the next five years in one evening, what would you insist goes on the list?

The word insist is doing the work. It gets past agreeable answers to the one or two things he is not willing to trade away.

From: Hypothetical Questions to Ask Boyfriend

We open a business together tomorrow. What is it, and what is my job?

The second half is the good half. The role he assigns you says what he thinks you are good at, and he will not have prepared that answer in advance.

From: Funny Hypothetical Questions to Ask Your Boyfriend

What's a boundary you need that you worry will sound like rejection?

An evening alone each week, a topic that's off limits with your mother, no talking the minute they get home. Naming the worry first is what stops it from landing as rejection.

From: Conversation Starters for Couples

If you woke up tomorrow able to do one thing brilliantly, what would you pick?

Listen for whether the skill is private or for an audience. Painting, public speaking and cooking suggest quite different things about what she wants more of.

From: Hypothetical Questions to Ask Your Girlfriend

What if I asked you to move somewhere with no job lined up for either of us? Could you do it?

Tests his tolerance for insecurity against his need for a plan. A firm no is not a failure of nerve; it is information about the conditions under which he can commit to something big.

From: What If Questions to Ask Your Boyfriend

What is the most you have ever spent on something for yourself?

It usually comes with an explanation about permission and guilt.

From: 1000 Questions to Ask Your Partner