Online dating and brand strategy—what do they have in common?

It’s 11:30pm, and I’m downing water to stave off tomorrow's hangover after a night out in SoHo. Kicking off my shoes, I settle onto the couch and start updating my WhatsApp group chat about my latest date.

“Did he ask any questions?” pops up as the first message.

Let’s call him Tom. Nice guy. Polite, punctual, good job, didn’t cross any lines—but no questions. I found myself, yet again, steering the entire conversation, filling the time with small talk, hoping to make it to the end without yawning.

Sound familiar? Many of us encounter this, both in dating and in business. We meet people who can talk endlessly about themselves but never take the time to truly engage us. The result? We leave the conversation feeling unseen and drained. On the flip side, the ones we interact with feel uplifted, perhaps unaware they’ve just held a one-sided monologue.

This isn’t just a dating problem—it’s a business one, too. Brands that fail to ask the right questions and actively listen to their audience can fall into the same trap. So, what can the world of online dating teach us about brand strategy? A lot, actually.

Let’s break it down into three core lessons for building better connections—whether in love or in business.

1. Ask good questions

What defines a “good” question? Good questions spark curiosity, invite deeper thinking, and encourage a meaningful exchange. For example, asking, “Are you reaching your target customers?” is fine, but asking, “What obstacles are preventing you from reaching your target customers?” opens up an insightful discussion. The second question encourages reflection on challenges and possibilities, leading to a richer dialogue.

In branding, asking the right questions is essential. Strategists and business leaders need to break things down: What problem are you solving? Why does it matter? Who are you trying to reach? These questions clarify your mission, streamline your strategy, and align your team behind a common goal.

2. Listen actively

   
   

We often mistake listening for a passive act, but active listening is one of the most important—and difficult—skills to master. In both dating and brand strategy, how you listen can make or break a relationship.

Active listening is the invisible thread that runs through effective communication, extending beyond merely hearing words. It’s about being fully present in the conversation, showing genuine interest, and responding thoughtfully. When you truly listen, you validate the speaker’s experiences, encourage openness, and build trust.

For brands, this means really tuning into customer feedback, team discussions, and market signals. Are you picking up on unspoken needs? Are you identifying misalignments before they become big problems? When you listen carefully, you gain the insights needed to make informed decisions that unlock, build, and protect your business.

Some tips for mastering active listening: put down your phone, make eye contact, ask follow-up questions, and don’t interrupt. Allowing silence can create space for deeper conversation, whether on a date or in a boardroom.

3. Aim to understand, not impress

   
   

One of the most common missteps in both dating and branding is focusing on impressing rather than understanding. Think of the overly confident finance guy on a first date who can’t stop explaining the intricacies of the stock market — even when no one asked.

Brands often do the same, coming into conversations with clients, partners, or investors with a rigid agenda. While it’s important to showcase your expertise, entering a conversation with the sole purpose of educating or pitching can stifle creative connections. The goal should be to understand, not just to sell.

When you approach a conversation—whether with a date or a customer—with curiosity, humility, and an open mind, you build rapport, establish common ground, and foster a deeper connection. In branding, this openness can lead to breakthrough ideas, stronger partnerships, and a more loyal customer base.

TLDR

Whether you’re navigating the dating world or trying to build a successful brand, the same principles apply: ask meaningful questions, listen actively, and aim to understand rather than impress. These simple but powerful strategies can improve not only your personal connections but also the way your brand connects with its audience.

Next time you’re out on a date—or in a business meeting—remember: it’s all about connection.

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Are you ready to build deeper, more meaningful connections with your customers? Let’s talk about how a strategic approach to branding can elevate your business. Reach out for a consultation today.

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