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,