Questions to Ask the Opposite Gender
Questions for getting to know a man or a woman you do not know well yet, whether a new friend, a coworker, or someone you are dating, written to stay away from stereotypes and to keep the exchange two sided.
The questions
Open any question for the note
What's taking up most of your week right now?
Why ask it
A better opener than asking what someone does, because it catches study, caring for a relative, a move, or a side project as easily as a job.
How did you end up doing that?
Why ask it
Almost nobody arrived at their current life in a straight line. The detour is the interesting part and it is easy to talk about.
What did you think you'd be doing at this age?
Why ask it
Candid without prying. The gap between the plan and the present is where people usually say something real about themselves.
What have you gotten better at recently?
Why ask it
Progress is easier to talk about than achievement, and it sidesteps the comparison that questions about success tend to invite.
What do you do with a free evening and no plans?
Why ask it
Shows how someone actually rests rather than how they would describe themselves. Answers are concrete and easy to follow up on.
What's a strong opinion you hold about something unimportant?
Why ask it
Playful and safe, and it usually produces the first real laugh of a conversation. Have your own answer ready.
What are you tired of being asked?
Why ask it
Useful and slightly disarming, and it stops you from asking the thing everyone else has already asked them this month.
What's something you'd like to be asked more often?
Why ask it
The natural pair to the previous question. It hands them the subject they actually want to talk about, which most conversations never reach.
When do you feel most like yourself?
Why ask it
Answers name a place or an activity rather than a mood. The follow up worth asking is what makes that setting different from the rest of their week.
Who do you talk to when something goes wrong?
Why ask it
Tells you how someone handles trouble and how close their circle actually is. A long pause here is itself informative.
What did you believe firmly five years ago that you don't now?
Why ask it
Shows whether someone can revise a position. Notice whether the change came from an argument, an experience, or one particular person.
What do you notice about how people treat you that they probably don't realize?
Why ask it
Better than asking someone to speak for their whole gender. It keeps the answer to their own experience, which is the only thing anyone can actually report.
What's a compliment that stuck with you?
Why ask it
Reveals what they want to be seen as, which is often not the thing people usually praise them for.
What are you saving up for, in money or in time?
Why ask it
Priorities in plain form. It works even when the answer is nothing, because the reason for that is usually the interesting part.
What's a risk you're glad you took?
Why ask it
Concrete and positive. Watch whether the risk was chosen or forced on them, since that says a lot about how they read their own life.
What do you do that you know isn't good for you?
Why ask it
Stays light rather than confessional if you answer first. Replies range from sleep to spending to a habit of agreeing to everything.
What would your closest friend say is your best and worst quality?
Why ask it
The indirect framing is what makes the second half answerable. People are noticeably more honest when speaking as somebody else.
What's something you got wrong in a friendship or relationship?
Why ask it
Ask later rather than early. A specific answer suggests self awareness; a story in which they are only ever the wronged party suggests rather less.
What would you want someone to understand about you before deciding they know you?
Why ask it
Direct without being heavy. It invites a correction to a first impression, which most people are keen to make if given the opening.
What do you want to ask me?
Why ask it
Ends the imbalance. A conversation where only one person asks questions is an interview, and the other person always notices.
Keeping the Conversation Even
Practical guidance for the conversation itself
Two Sided by Design
Answer your own question
Ask, listen, then give your own answer briefly before asking the next thing. Without that, twenty questions in a row reads as an interrogation however warm the tone.
Follow one answer instead of moving on
Most of what is worth hearing arrives in the second or third layer. "What was that like" and "what did you do next" get further than a new question would.
Let them steer
If they take a question somewhere unexpected, go with it. The topic they choose tells you more than the topic you planned.
Read the Setting
At work
Questions about hobbies, opinions, and how someone ended up in their field are fine. Questions about relationships, appearance, or what they want in a partner are not, regardless of intent.
On a date
The harder questions about past relationships and self awareness belong late in a first conversation or in a later one. Front loading them puts the other person on the back foot.
A new friendship
Pace matters more than depth. One searching question per conversation, with real listening around it, builds faster than a run of them at once.
What to Avoid
Asking someone to explain their gender to you
Questions like "why do women do this" or "what do men really want" ask one person to speak for millions. Ask about their own experience instead and you get an answer worth having.
Treating an answer as representative
One person's view is one person's view. Generalizing it back at them, even approvingly, is the fastest way to make them stop being candid.
Compliments that arrive mid question
Slipping flattery into a question changes what is being asked and usually gets a polite answer rather than a true one. Keep the two separate.
Pushing when someone deflects
A joke, a short answer, or a change of subject is a boundary. Note it and move on; asking again in a different form is still asking again.