Storytelling Tips to Make You a Better First Date

The Power of Great Questioning

Sharing your point-of-view is an important part of being a small business owner where clients often work directly with you, the human. And while I’ve never shied away from sharing my point of view on being a #femalefilmmaker, or a woman entrepreneur, there is one point of view I haven’t shared much of…being a single woman working as a storyteller in the wedding industry. 

This post isn’t about weddings (though I will likely write more on that in the future). It is about an important lesson I’ve learned at my day job, and how it can help improve the quality of a first date.

Here’s a personal look through the lens of three first dates I’ve been on recently.


First Date #1 began sitting across the picnic table from one another at a local brewery with a lot of small talk. I started by asking questions like ‘What do you do?’, ‘Where are you from?’, ‘How long have you been living here?’, and for the next three hours (with a venue change about halfway through) we talked about everything from his recent move to Raleigh, to his previous job and travels around the world, to his future career aspirations and his ex-girlfriend. Oh, his ex-girlfriend. I learned lots about her. At one point I even joked that she and I were now on a first-name basis as he transitioned from referring to her as ‘his ex’ to using her real name. This was especially ironic because I was fresh out of a four-year relationship, and this caused a fair amount of anxiety leading up to this particular date. Was it too soon? Would I have to talk about it? How much would I have to share? Turns out I didn’t have to worry about any of that, as we had lots of ground to cover on his last relationship. Though, to be fair, I can’t really blame him.  While he was certainly forthcoming with information when I asked, I was definitely driving the conversation by continuing to follow up with more and more questions.

That’s the thing. I’m a video storyteller by day, and you only learn the story if you ask questions. And then you follow those questions with a lot of listening. When we pre-interview subjects before shoot day the name of the game is listening. Time I spend talking about myself is wasted time, as it contributes little to the project or story at hand. Yes, rapport is important and my intention is never to interrogate, but in my experience genuine interest and thoughtful follow-up questions can build as much rapport as sharing your own personal stories, while still keeping the focus on the subject and the story you’re trying to tell.

When it comes to dating, as opposed to making a film, questions serve two main purposes: 1) to drive conversation and 2) to get to know the person sitting across the table from you. The more information you have, the more quickly you can figure out if they’re a good fit for you.

This can become challenging, however, when the other person does not have the same curiosity or skillset to do the question asking. The conversation can begin, and stay, one-sided if only one person is asking the questions.

You might think this is uncommon for a first date to be so lopsided with regards to conversation, but I have recently discovered that it is not. And while during the day working with clients I am 100% comfortable with being the one to drive the conversations, when it comes to dating it’s hard not to feel overlooked when it’s goes un-reciprocated.

Let’s go a step further. Beyond just being willing to ask the questions, the next challenge is asking the right questions. First Date #2 was again over beers, this time at a bar right near the #bdlbstudio, and about 30 minutes in he transitioned to asking me some questions… (good sign!)

Where are you from originally?

Where did you go to college?

What brought you to NC?

Good small talk questions (remember, this is where First Date #1 started… covering the basics first is a must before diving into something deeper), but eventually without strong follow up questions the conversation they led to was more like a factual timeline of my life that left a lot of the important stuff out. At one point he asked about the key players in my family and after I shared about everyone in my family except my mom, he never asked about her.

I think I know where this comes from. I’m sure he noticed that she wasn’t mentioned, but he felt uncomfortable asking about it. ‘Did something bad happen?’ Does she not have a mom?’ ‘Are her parents divorced and on horrible terms?’ ‘I don’t want to make her uncomfortable by asking her about it.’ (The real answer is that my mom passed away in 2016 after a 7 year battle with breast cancer.)

I can appreciate where that hesitation comes from, but I genuinely believe that our fear of being ‘too nosey’ often prevents us from asking the good and important questions that let the other person know you’re listening, that you’re interested in them, and that you want to know more. You can always follow the ‘nosey’ question with a quick ‘Please let me know if you’d rather not talk about that’ to prevent the feared discomfort we might create, though I suspect they might not take you up on it. I’ve been using this line pretty regularly for the last year and no more than two people have ever taken the pass. This very official research data reinforces my belief that we’re all waiting to be asked the important questions, and there’s a lot of valuable information out there, right under the surface, that will likely never see the light of day unless someone asks them. And not just any questions, but the right questions.

In interviewing people for the films we make, these questions are what take a film from okay to good, and hopefully to great. Great stories that truly connect us as people always go deeper than the who, what, where and when.  The great stories are made by the follow-up questions. How are we getting our main characters to go to the next level where they explore and articulate the nuances of who they are, what drives them, how they’ve changed over time… you get the idea. When thinking about the second purpose of questioning on a date, (getting to know the person and whether they’re the right fit for you), isn’t this the most crucial part? I ultimately don’t care where you grew up or where you went to school; I want to know how those experiences shaped who you are now, and the way in which you interact with the world.

More than upping the odds of a successful first date, this is the reason I really feel so strongly about this topic. There’s no feeling like the one you get when someone sitting across from you SEES you. The parts you want people to see, but you’re not quite sure how to show them. The parts that don’t often get uncovered until someone cares enough to do a little digging. And even when they have the desire and curiosity to do the digging, do they have the skills?

Let’s look at a couple examples of common questions I’ve asked/been asked on a first date and see where you could take them and go a bit deeper…

EXAMPLE 1: Where are you from?

  • What was your experience like living there?
  • What is your relationship like now with that place?
  • Have you ever thought about moving back?
  • When you go back to visit now, where are the first places you go?

EXAMPLE 2: What do you do?

  • Were there signs from your childhood that this is what you’d be doing?
  • What keeps you motivated?
  • What are you missing most from the work you’re doing right now?
  • Where do you envision your career 5 years from now?

EXAMPLE 3: Where does your family live?

  • How often are you all able to spend time with each other?
  • What does that usually look like?
  • Who are you closest with?
  • How has your relationship with them (parents and/or siblings) changed as you’ve gotten older?

Ending on an optimistic note, every now and then I meet my match in terms of questioning and conversation. First Date #3 took place on the rooftop of Grub, a local restaurant, on a slightly overcast and potentially rainy Sunday morning following a late night of importing wedding footage. It was less than 10 minutes into breakfast when he insisted that he get the chance to ask some questions too. This happened several more times as he continued to work hard at getting to know me over the next couple of hours. Several things were noteworthy here.  1) Not only was he doing the work of asking the questions, but he regularly went beyond the easy surface level question.  2) He listened. Like really listened.  This particular trait is so uncommon that a couple  of times when he didn’t respond right away I was caught off guard; I have become so used to people jumping in right after I finish talking to relate it to their own experience that I forgot what it felt like to have someone really listen and process what I said.

During our conversation, following a fairly personal question on my part (#nosuchhthingastoonosey), he replied “If I answer that it’s like you’re seeing more of me than 99% of the people in my life. It takes this from a first date to a more intimate place. It’s what’s so great about relationships.’ He articulated so beautifully the powerful part of both dating and great storytelling; when you ask the right questions it allows you to get to know people intimately. It allows you to see the real story, the heart driven part, and not just the peripheral shit.

So friends, if you take anything away from reading this (besides the fact that I’m a difficult first date), take this. Don’t be afraid to ask the questions. Even when it feels nosey, or inappropriate. And, learn how to ask good questions. The ones that go beneath the surface. It’s okay and important to start with the easy ones, but learn how to follow up from there. Perhaps your nosey question is just the one they’ve been waiting to be asked.