Relationship questions for partners at every stage

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 Your Boyfriend

How do you want us to keep dating each other, however long we're together?

If she asks for a real date once a month, make it a rule and put the first one on the calendar now. If it's flirting by text from the next room, start before you go to bed.

From: Romantic Questions to Ask Your Girlfriend

When I ask what's wrong and you say "nothing," what would you like me to do next?

Sometimes "nothing" means nothing, and sometimes it means "not yet." Have him pick the follow-up that works on him: drop it, come back in an hour, or sit nearby and wait. Then tell him what your own "I'm fine" usually means.

From: Deep Questions to Ask Your Boyfriend

What if we could have one of our arguments over again? Which one, and what would you do differently?

Keep this for a calm evening and go second. When your turn comes, name what you would change in yourself and leave out what you wish she had done.

From: Hypothetical Questions to Ask Your Girlfriend

What do you think my biggest flaw is, and how does it show up between us?

The second half keeps it from turning into a character assessment. 'You're stubborn' is hard to use. 'You're stubborn, so I've stopped suggesting restaurants' gives you something to fix. If she won't name one, lower the stakes and ask for a medium-sized flaw.

From: Questions to Ask Your Girlfriend About Yourself

What's the fastest way to make me laugh when I'm in a bad mood?

If he has an answer ready, he's been studying. If he doesn't, give him one, because it's among the handiest things he can know about you.

From: Fun Questions to Ask Your Boyfriend