Questions to Ask Your Boyfriend
The things he would tell you if you asked properly.
- Players
- 2 players
- Length
- 20–40 min
- Cost
- Free · no signup
- Long distance
- Works long distance
Ready?
The things he would tell you if you asked properly.
- Players
- 2 players
- Length
- 20–40 min
- Intensity
- Sweet
Free · No signup · Nothing you answer is saved
How do you play Questions to Ask Your Boyfriend?
Good questions to ask your boyfriend are specific rather than general — "What is something you are under pressure about that you have not mentioned?" gets a real answer where "Are you okay?" gets one word. Ask one at a time, answer them yourself too, and let the pause after each answer sit rather than filling it.
How to play
- Ask one at a time. Do not work through it like a list.
- Let the pause happen after the answer. Do not fill it.
- Ask one follow-up, then leave it there.
- Answer them yourself too — a one-way session becomes an interview fast.
- Six questions is a good evening. Come back to the rest another time.
Why couples love this game
The specificity does the work. "Are you okay?" is answerable with one word and usually is. "What is something you are under pressure about that you have not mentioned?" is not — it names a category, and once a category is named the answer tends to come out.
Most men have a much shorter list of people they can say anything to than their partner realises. Often the list is one person long, and it is you — but only if you ask something he can actually answer.
These questions are built for that. They avoid the two failure modes: the vague check-in that gets "I'm fine", and the interrogation that makes him defensive. Everything here is specific enough to answer and open enough to be interesting.
They lean toward the things men are least often asked — what he is under pressure about, who he can talk to, what he thinks he is supposed to be.
Example questions
- Who is the one person besides me you can say anything to?
- What is something you are under pressure about that you have not mentioned?
- When did you last feel genuinely proud of yourself?
- What do you think you are supposed to be, and who decided that?
- What is something you wanted to tell me this month and did not?
- Which of your friendships do you wish was closer?
The full game has 40 of these, shuffled every time you play.
Who this game is best for
- Couples where one of you talks more than the other
- A quiet evening with nowhere to be
- Long-distance calls
- Anyone who keeps getting "I'm fine"
Tips to make it better
- Do not ask these in the middle of an argument. They are not a tactic.
- Answer them yourself. Reciprocity is what makes it safe.
- Do not fix what he says. Sitting with it is the whole point.
- If a question gets a short answer, move on rather than pushing. Come back later.
Frequently asked questions
What are good deep questions to ask your boyfriend?
Ones that name a specific category rather than asking generally. "Who is the one person besides me you can say anything to?" works because it has a real answer he has probably never said out loud.
How do I get my boyfriend to open up?
Ask something answerable, then stop talking. The two things that shut a conversation down fastest are a vague question and filling the silence before he has finished thinking.
How many should I ask at once?
Six or so. Working through forty in a night turns a conversation into a questionnaire, and he will notice.