Asking Questions With Heart Behind Them

As a society, we have become so habitual and robotic in what we ask conversationally in social ­­situations. We ask really open ended questions, perhaps to allow the respondent freedom in how they answer, but I really suspect it is because we have gotten to be, well, rather shit at personalizing our questions.

Whenever I am in a ­­situation, for example, where I see someone for the first time in ages, I never know how to answer a very basic, universal question: “What’s new?” Let’s see. A nephew was born. I was promoted. I had some upgrades done in my kitchen. I got new a heating and air conditioning unit. I PR’ed my squat clean. I went to Bali. I went to Malaysia. I went to Mexico. I went to Guatemala. I have managed to keep a house plant alive for the last 6 months. I have been growing a lot spiritually. I started collecting vintage tea cups. I took a writing class. Oh? You were just asking, am I well and not in distress?

One of my biggest triggers is feeling like I am being asked questions off a checklist, like there is no heart behind them. It’s just an obligatory, polite adult thing to do.

“How’s work?”

“Same old. Stressful”


“How’s your condo?”

“It’s good.”


“How’s CrossFit?”

“it’s awesome.”


When it comes to work, I am appreciative for my career and all that it teaches me about who I am and the leader that I strive to be. If you ask me about work, ask me because you want to know those things more so than you care about learning that my title changed to Associate Director. If you ask me about my condo, ask me because you want to know how fulfilled it makes me to be able to be a homeowner as a single woman, that it is something I acquired all on my own. Ask me because you have respect that I did it without financial help from family or a man. You should care more about that than the new lighting I had installed. If you ask me about CrossFit, ask me because you really respect that I have such a passion in life. Ask me how my journey has been now that I am injury free. Ask me about CrossFit because you are in admiration that I can get my ass out of bed every morning to grind hard. Don’t ask me because it’s just this “thing” I do.

When it comes to superficial conversations, I reserve those for water cooler chat or random encounters. I was once insulted when a friend told me I am “particular”, but I then came to take this as a compliment. It reflects that I put thought into my choices, which include who I spend my time with. So if I choose to spend time with someone, right or wrong, I have an expectation to find some common ground and connection. Call me hippy dippy but I am far more fulfilled when I do feel that connection. I do not expect everyone I talk with to take questions to the next level, but at the very least, have sincerity and heart behind conversations. Otherwise, just smile and move on. I am ok with that too.

I want to walk away from conversations feeling entertained, enlightened, inspired, even a bit smarter. I am sure anyone can argue that I do not need to rely on people asking the “right” questions for me to feel connected or validated. I agree to an extent. To me asking questions shows the other person’s interest. I do not want to talk about spirituality to someone whose eyes are dulled with an expression of “please make this conversation end”. I take questions, and the right questions, as an invitation of interest. It does validate to me that people want to know me, they want to understand me and they want to catch up with me. We have all been in situations where we are talking and the other person is “uh huh”ing and “right”-ing without even listening to what you are saying. It’s the same defensive feeling we may get in scenarios where we feel like the other person rather be elsewhere because they are not stimulating conversation.

I realize this blog may make me sound needy or even indignant. So be it. This has been a tough one for me to post (I’ve been sitting on it for days). I know though I am not alone in having these thoughts and as always, I welcome feedback, whether it’s tell me to chill out or to tell me you too have been there.