3 Leadership skills for your dating life

Create more meaning and connection

5-minute read

Side effects of a meaningful dating experience might include:
  • Self-confidence
  • Engagement
  • Empowerment
  • Fascination
  • Learning about someone new
  • Deeper exploration
  • Laughter
  • Not taking yourself so seriously

Invest in yourself and your dating life? Sounds like a win-win! This Swipe Season (January 1- February 13), whether you’re navigating the dating scene, in a relationship, or somewhere in between, these tips will help you cultivate deeper meaning into your love life.

At LifeLabs Learning, we teach life’s most useful skills. These are small changes that lead to big impact. We focus on leadership skills in the workplace, but we’ve also seen that these skills tip over into everyday life. Three leadership skills in particular can make a big impact on your dating life. With these skills, you hold the power to engineer more meaningful dating experiences every time.

Choose curiosity

Ever been on a less-than-fascinating date? Perhaps you deem your date “boring” or “basic.” But what if you shifted your mindset, and instead of viewing this person as a potential life partner, hookup buddy, or something in between, you chose to get curious instead? At LifeLabs Learning, we’ve studied the power of “q-stepping,” or defaulting into question mode. We found that the average person asks two questions in a 15 minute interval. Take a guess: how many questions do you think the best leaders and influencers ask in this same timeframe? Wait for it… 10 questions! So, next time your date shares something that sparks an intrinsic eye roll, challenge yourself to choose curiosity, and ask a question first. You might be surprised by what you find!

To take it a step further, ask open questions (e.g., “what” or “how” vs. “is” or “does”). Let’s say your date expresses interest in the game Settlers of Catan. Instead of inferring that your date is a nerd, get curious. What if Settlers of Catan isn’t nerdy at all (or maybe you are nerdier than you thought)? Here’s how it might play out:

  • Closed question: “Isn’t Settlers of Catan kind of nerdy?”
  • Open question: “Oh, I’ve never played Settlers of Catan! What do you like about it?”

What feels different about the open question? The biggest differentiator is authenticity. Nobody wants to be judged on a date. Half the time, it’s hard enough to simply show up and be yourself! Plus, an open question allows for a variety of responses (not simply a yes/no), which leads to more spontaneous and thought-provoking conversations. My challenge to you is to choose curiosity. View your date as an exciting opportunity to learn something new. You might walk away with some knowledge nuggets, at the very least, and perhaps even a love of a new board game.

  • Here are some curious questions, to get you started:
  • What were the top three highlights of X?
  • What’s important to you about X?
  • What do you like about X?
  • How did you get into X?
  • What are you most looking forward to this week/month/year?
  • What most surprised you about X?
  • How would you rate X on a scale of 1-10?
  • What was your most valuable takeaway from X?
  • Bonus: for every question, ask at least one more follow up question.


Picture this: Your date is late and hasn’t responded to your last text. You’re checking your phone every couple of minutes. Now you’re making up scenarios about what caused the delay. Maybe their phone died. Maybe they got stuck at work or had another obligation. Now you’re worried they’re busy, which means they won’t prioritize you now and perhaps never. Finally, you arrive at “my date doesn’t like me, they suck, and I’m unlovable.” That is a lot to derive from one delayed text!

This thinking pattern is known as the Ladder of Inference, coined by Chris Argyris. The Ladder of Inference looks like this: I collect a piece of data, for example, a missed text. When I don’t hear back from my date, I start to bring my own stories into the mix. Instead of seeing a missed text as a missed text, I eventually deduce this to mean the person sucks, and I’m unlovable. At this point, I’m working up a sweat because I am rapidly ascending the Ladder of Inference! Yikes!

According to Stefnie Howley, Date Coach at our client, Match: “I am unlovable, unworthy, broken, or unwanted” are common stories that a person might bring into their dating life. What if we reframe instead? By tuning in and noticing when we’re climbing the Ladder of Inference, we’re able to reduce attachment to old narratives and separate pieces of information as objective data-points. To reframe, pause and ask yourself these questions:

  • What is the data in this scenario?
  • What stories and narratives am I bringing into my conclusion?
  • Where am I on the Ladder of Inference?
  • How else might I interpret what’s going on?

Worst case scenario, if your date never shows up, you can still get value out of the experience by reframing and asking: “what can I learn from this?”

To quote another one of our lovely clients, Tinder, “despite how it feels, rejection is often not personal. It can, in fact, serve as an opportunity to examine patterns and reframe a situation.”

Engineer surprise

We’re passionate about the power of surprise at LifeLabs. Thanks to neuroscientist Wolfram Schultz, we know that surprise amplifies emotion by 400%! Say what? So, how do we harness this powerful tool to create a more delightful dating experience?

  • Build anticipation: Excited about a date? Good news, you can extend the pleasure of the experience by building anticipation. Create a countdown, set time aside to get ready, and embrace the lead up. You might treat yourself to a new article of clothing, accessory, or self-care routine (like a workout class, candle, or new tune). “It’s important that we take care of our own wellbeing, heart, mind and soul before entering into the next relationship,” notes Stefni Howley. As an added bonus, this prep time can add to your self-confidence, too!
  • Activate the senses: Dating is an opportunity to explore someplace new, with someone new! Best of all, dates are opportunities to create experiences. Authors Joseph Pine II and James Gilmore point out that there is vast spectrum between a forgettable commodity (like a cup of coffee to-go), a service (coffee at a diner) and an experience (walking through the park on a chilly afternoon, with a warm cup of coffee in your hands). Coffee is the common denominator in these three scenarios, but the experience creates a rich, meaningful, and memorable date. To create an experience, invite more of your senses to the date! Wear something you love, eat slowly, listen to music together, take a whiff of your drink, and… I’ll leave touch to your imagination.
  • Bury a cookie: Not an actual cookie, although this would certainly be a surprising twist. I wouldn’t object if someone brought me a cookie on a date. What I mean though is a metaphorical cookie, something that will grab your date’s attention. It could be a pin that’s a family heirloom, a textured hat, or a rose. Something unexpected that might add a tinge of delight and interest during your date. Then, when your date notices this standout item, you can share not only a story behind it, but why it is meaningful to you!

Whether you’re self-partnered, actively dating, or in a relationship this Swipe Season, give these three leadership tools a try. If your date doesn’t text, ghosts, or things don’t go as planned, you can rest easy knowing you created a meaningful experience. Isn’t that empowering? Plus if being a better leader can make you a better dater, it can also work the other way around. Every date is an opportunity to connect and to grow as a person. Now, get out there, and get curious!