Questions to Ask Your Boyfriend: Ideas for Real Talks

Good questions to ask your boyfriend are open, specific and asked with real curiosity. They can't be answered with a yes or no, and they lead to a story. Below you'll find more than forty, sorted by mood, plus a few notes on how to ask them so it becomes a conversation and not an interrogation.

Why questions to your boyfriend can be hard to ask

Many men don't volunteer much about feelings. That's a stereotype with some truth to it, but not a law of nature. Often it's simply that nobody asks them in a way that leaves room for the answer. "All good?" leaves room for a "yes." "What annoyed you most today?" leaves room for a story.

A few things help, however your boyfriend is wired:

Ask on the side, not head-on. While cooking, walking or in the car, it's easier to talk than sitting across from each other on the couch.
Ask just one question at a time and allow pauses.
Answer yourself, too. If you only ask, it feels like an exam.
Don't judge the answer. If he tells you something that surprises you, ask: "What was that like for you?"

If he responds to direct questions with a shrug, try a detour. Tell a small story from your own day first, then ask: "And you?" Or suggest something you can do on the side, like a walk where you go side by side and don't have to look at each other. Many people start talking on their own then, without it looking like a conversation. What matters is that you aren't offended if the first try goes nowhere. By the second or third time, he'll notice you mean it.

Light questions to warm up

For evenings when nobody wants to dig deep.

What food would you eat for the rest of your life if you could only have one?
Which totally ordinary moment with me has stuck with you, even though nothing special really happened?
Which show have you secretly watched without telling me?
What talent do you wish you had that you don't?
What was your most embarrassing moment in school?
If you had tomorrow off and it cost nothing, what would you do?
Which song from your teens do you still know by heart?
What did you spend the most money on as a kid?
Which everyday habit of yours is the weirdest?
Which place in your town is secretly yours, and how did you find it?

Questions about the two of you

This gets more personal, but still pleasant.

What was your first impression of me, and what has changed since?
What do we do together that would be less fun for you alone?
When did you last think: I'm glad we're together?
What do I do that secretly makes you smile?
What would you like to do with me more often?
Is there something I see as smaller than it is for you?
What do you want from me on stressful days: quiet, distraction or closeness?
Which trait of mine do you see as a strength that I might overlook myself?
How do you notice I love you without my saying it?
Which topic do we avoid even though we should really talk about it?

You'll find more on how people show and receive affection in the guide to love languages.

Questions about his life and feelings

If your boyfriend tends to hold back, these questions need quiet and a good moment.

What has cost you the most energy lately?
What are you proud of that nobody knows about?
What did you need as a child that you give yourself today?
What are you afraid of that you rarely say out loud?
What do you expect of yourself that maybe nobody else demands of you?
When did you last feel misunderstood?
What was it like at your house when someone was sad?
Which decision in your life would you make differently today?
What do you need to wind down after a bad day?
What did your father or another man in your life model for you that you don't want to pass on?

If something comes up that weighs heavy, like recurring fears, grief or hopelessness, that doesn't mean you're doing anything wrong. It does mean it's worth talking to a therapist, a counsellor or a support service.

Questions about the future

What does a good ordinary Tuesday look like for you in five years?
What do you want to prove to yourself in the next few years?
Where would you like to live if money didn't matter?
What would be a sign to you that we're doing well as a couple?
How do you picture family, and what belongs in it?
Which trip do you absolutely want to have taken?
What would you do for work if you weren't afraid of failing?
What would matter to you in old age that we should already nurture today?

You'll find more inspiration in the future questions for couples.

Funny and slightly cheeky questions

Which of your quirks would you never criticize in me, because I find it endearing?
If we had to plan a heist, who of us would play which role?
What lie do you tell at parties when someone asks what you do for a living?
What's the dumbest thing you've ever googled?
What was your worst haircut, and is there photographic evidence?
Which of my friends do you secretly find exhausting?

For the last one, better to ask first whether it's allowed.

How to ask the questions in daily life

One an evening is enough. If you ask ten questions a day, it feels like an interview. One good question at dinner that you both answer brings more.

Hold off on "why." "Why" quickly sounds like a demand to justify. Better: "What was that like?" or "What did that do to you?"

Remember what he tells you. If he notices in three weeks that you remember an answer, it's worth more than the question itself.

Leave room for no. If he doesn't want to talk one evening, that's fine. Say: "Then I'll ask you again next week."

If you want to make it easier

Many couples plan a conversation like this and forget it after two days. That's rarely a lack of love, more a matter of daily life. One option is to automate the question: with Us2 you get one question a day for two, you answer separately, and afterwards you see what the other wrote or said in a voice message. For men who prefer to think before they talk, that's pleasant, since nobody is waiting directly for an answer.

For more conversation material, there are the questions to ask your partner and the deep conversation questions.

Quick takeaways

The list is not a program you have to work through. Pick two or three that fit your evening, ask one of them today and listen without already having the next one in your head. The best question is the one you're really interested in.

If you want a daily prompt for it, take a look at Us2: one question a day for two, three days to try with no payment details.