27 Qualifying Questions To Reveal His True Character

How do you get to know someone’s true character? I’ve recently had a consulting client and in our last session, we went over questions she could ask while on a first date. The idea was to ask insightful, open ended questions that would allow for good conversation as well as getting to know someone new. We discussed, outside of a few basic criteria, how asking mindful questions could help gain insight into someone’s personality and values and how they measure up to our own values and what we desire in a potential partner. Another advantage to having an arsenal of thought provoking questions to ask is that it helps you get out of your head on worrying about if like you and instead focus more on whether or not you like them.

When I say ‘an arsenal of questions,’ I mean that loosely. Of course, the goal is to keep the questions as organic and conversational as possible. You don’t want go firing off questions one right after the other. It’s not an interrogation or job interview.  Also, it’s a good idea to avoid asking anything too heavy that might make them uncomfortable or bring the mood down. My client and I came up with a unique list of questions for her and her date, but it got me thinking about others.

In the coaching space, one of the main techniques used is ‘powerful questioning.’ A powerful question provokes you to think deeply and to engage in conversation with others that leads to a deeper understanding and connection. I got to thinking, what powerful questions could you ask in the beginning stages of a relationship that could help reveal more of someone’s personality and character?

You want to keep most of these questions light hearted and fun, for the most part. When they answer, you’re not just listening to what they say, you’re observing their eye contact, body language, and vocal tone.  The goal here is to begin to discover a bit more of who they really are, but these questions and answers can’t accomplish that by themselves. Really getting to know someone takes time and experience with them.

Some of my own ideas…

What do you think about dating a woman who makes more money than you?

What steps have you taken to improve your relationship skills?

What 5 male characters from movies are your favorites and why?

Tell me about your relationship with your mom.

Do you think crying is a sign of weakness or strength?

Would you rather be married or spend the rest of your life single?

What would you do differently if you knew no one would judge you?

What stands between you and happiness?

What do you want to be remembered for?

What has been your biggest challenge in past relationships?

Who are your role models in life?

What has been your greatest accomplishment so far?

What was the most difficult thing you’ve ever gone through?

How would others describe you?

What have you always wanted to change about yourself?

If  you had the chance to change the world, what would you do?

What’s your dream job?

What does romance mean to you?

What are your views on marriage?

How do you have fun with a partner?

What are your thoughts on Valentine’s Day?

What does femininity and masculinity mean to you?

What qualities do you find attractive in a woman?

What does intimacy mean to you?

What does a relationship mean to you?

How would you work through disagreements with your partner?

What is your love language?

Some of these might seem random, but these are the type of questions that will give insight into his values and what’s important to him. They also tell you about his past, present, and projected future as well as the the lens in which he views himself, others, and the world. However, it goes without saying that the best way to find out someone’s true character is to give it time. Actions speak louder than words, but questions like these do help. What questions can you think of that might help you get to know someone’s character?

If you would like more help with a dating and relationship issue, I am now accepting new clients for 1:1 consulting. For more info, check out the consulting tab up in the main menu bar and from there, you can fill out the application to get started working with me privately.

Until next time,

Ash Pariseau


  1. These are good questions and you should definitely want to know the answers to them in the context of a long term relationship. And I can certainly see why a woman who is primarily interested in a LTR would find them useful. In the case of a first date however, you are not likely to get real answers to many of them. On a first date any man with any kind of experience with women is going to just make up something that sounds good and keeps him out of trouble. Most men are able to suss out which questions when answered truthfully will only serve to hurt his chances in the dating process. To be fair there are a few of these questions that are first date appropriate, but most of them are landmines to be avoided or answered in a general and superficial way and quickly change the subject. I wouldn’t even answer truthfully to some of them until we had been dating for months or it was clear that our life outlooks match up at least 95%.

    I fully endorse this list before getting into any kind of major commitment though. They could help surface major philosophical differences in outlook, if they are answered truthfully.

    FWIW I am a man who is very happily married for 35 years. But I dated a lot as a young man

    • Thank you for adding your perspective. You make a good point about the difference between questions to ask on a first date vs within the context of a longer term relationship. I’ve been in a long term relationship for so long, it’s just where my head is. I actually might want to edit for clarity around that.

      • I have to agree with Clever User Name. The technical term for those questions is an assessment. A lot of guys won’t recognize them as an assessment but some will.

        If you ask them, you better be able to accept an answer you don’t want to hear and be willing to answer the same questions.

        I’d probably answer “What 5 male characters from movies are your favorites and why?” on a date. I probably wouldn’t answer, “Tell me about your relationship with your mom.” on a date. Then, again, if I made the snap decision that I don’t want to see her again, I might. I might tell her that my mother was a raging alcoholic who should have been in jail for domestic violence, put a coffee cup through a kitchen window aiming for my father’s head, and took off when I was 7 (all true.) But, hey, you asked.

        We wouldn’t be ordering dessert.

        In your last post, you talk about Boundaries. You’re not the only person who gets them. These questions push boundaries.

        You ask them and somebody could come back at you hard. If they liked you before, they might not like you after. There’s a fine line between assertive and obnoxious and depending how much finesse you have, you could find yourself on the wrong side of that line.

        You could step on a lot of mines asking these. Tread lightly when you ask.

  2. ““What 5 male characters from movies are your favorites and why?”

    Rhett Butler (Clark Gable) “Gone with the Wind” – “Why? Maybe it’s because I’ve always had a weakness for lost causes, once they’re really lost.”

    Rick Blaine (Humphrey Bogart) “Casablanca” – “If that plane leaves the ground and you’re not with him, you’ll regret it. Maybe not today. Maybe not tomorrow, but soon and for the rest of your life.”

    Hawkeye Pierce (Donald Sutherland) “M*A*S*H” – “Who am I? I am the pro from Dover, and this [Indicates Trapper John] is my favorite caddy.”

    Oddball (Donald Sutherland) “Kelly’s Heroes” – “Why don’t you knock it off with them negative waves? Why don’t you dig how beautiful it is out here? Why don’t you say something righteous and hopeful for a change?”

    Bruno Stachel (George Peppard) “The Blue Max” – “Perhaps it’s force of habit. In the trenches, we couldn’t even bury the dead; there were too many of them. I’ve never had the time to discuss them over a glass of champagne.”

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