To Ask Or Not To Ask...

I’ve always been a bit of an over-sharer.

Not in the “let me tell a complete stranger my entire life story in the grocery store checkout line” kind of way. (Okay… maybe occasionally.) But I genuinely enjoy talking about my life. I like sharing stories, experiences, opinions, memories, and all the strange little things that have made me who I am. And even more than that, I love when someone is curious enough to ask.

I know personal questions can be a tricky thing on a date. There are plenty of people who would rather keep things light, especially when they’re first getting to know someone. Questions about relationships, fears, childhood, dreams, regrets, or the complicated chapters of someone’s life can feel intrusive when you haven’t known each other very long. It’s important to be respectful of each individual person’s boundaries. I personally know that most ladies would not appreciate being asked something like “ what’s the craziest thing you’ve ever experienced?” or asking details about an industry that can be very tightly under wraps. 

For me, though? You can ask me the personal question. In fact, there’s a pretty good chance I’ll be delighted that you did.

Curiosity Feels Like Connection

One of my favorite parts of spending time with someone is that moment when the conversation stops feeling like polite conversation and starts feeling real.

We’ve moved beyond where we’re from, what we do for work, or what we ordered for dinner. Suddenly we’re talking about something that actually tells me who you are or gives me the opportunity to show you who I am. Those are the conversations I remember.

Ask me what I was like when I was younger. Ask me about something I’m afraid of, something I’m proud of, a relationship that changed me, or a decision I’d make differently if I could. You can ask me about my childhood, my relationship with my parents, or why I chose the path that I did. Ask me about the industry and my experience in it. Ask me why I think the way I do.

There are very few subjects I consider completely off-limits when the question comes from genuine curiosity. And I think that’s because, to me, sharing is one of the ways I create intimacy.

There’s a Difference Between Personal and Invasive

Of course, being open doesn’t mean boundaries disappear.

There’s a huge difference between someone asking a personal question because they’re genuinely interested in understanding me and someone interrogating me because they feel entitled to information. I think you can usually feel the difference.

Curiosity leaves room for someone to say, “I’d rather not answer that.” It follows the conversation instead of forcing it. It feels warm rather than transactional.

And when that’s the energy behind the question, I rarely find myself offended by it. If anything, I appreciate it.

I’d much rather someone ask me something interesting, unusual, or unexpectedly deep than spend an entire evening carefully avoiding anything that might be considered “too personal.”

My only request, is that you are prepared for the answer I give you. I have had plenty of people think that they’ve wanted the answer to a burning question in their mind, but when I answered it, they found that it ruined the experience for them. So please, only ask questions that you are certain you want the honest answer to.

I Want to Know You, Too

This goes both ways. If I’m asking you questions, it isn’t because I’m conducting an interview. It’s because I’m fascinated by people.

I want to know what makes you light up. I want to hear the story you don’t normally get an excuse to tell. I want to know what you could talk about for three hours if someone would just give you the opportunity. I want to know what has shaped you.

There’s something incredibly intimate about realizing that a person trusts you with a piece of themselves that doesn’t come up in everyday conversation. Maybe that’s why I’ve never completely understood the idea that certain questions are automatically “too deep” for a first date.

If we somehow end up discussing the meaning of life before the appetizers arrive, I’m probably having a fantastic time.

So, ask me...

If you’ve ever been on a date with me and found yourself wondering, Is this too personal to ask? You can probably ask.

I may laugh. I may give you a much longer answer than you were expecting. I might tell you a story that sends us down an entirely different conversational rabbit hole. Every once in a while, I might tell you that there’s something I’d prefer to keep to myself, but I’m probably not going to be offended that you were curious.

Because ultimately, I don’t want our time together to feel like two people carefully performing the safest possible version of themselves. I want stories. I want curiosity. I want tangents and unexpected confessions and conversations that somehow become much deeper than either of us intended.

So skip the small talk if you want to.

Ask me something real.

"When we're brave enough to risk a conversation, we have the chance to rediscover what it means to be human." — Margaret Wheatley