Today, on my way home from an important company event, I passed through the central station of Basel, the city where I live. Watching couples reconnect in front of the station entrance—some rushing into each other’s arms, others just quietly walking side by side—I found myself reflecting on an analogy I had casually used earlier in the day during a group discussion: I compared dealmaking to dating.

At first, it felt like just a spontaneous remark—maybe a clever way to illustrate a point, nothing more. But the thought lingered. The more I considered it, the more the analogy started to make real sense. Not just in a lighthearted or playful way, but in how both dating and dealmaking expose the same core truths about human behavior: how we communicate, how we build trust, the energy we bring, and how we navigate uncertainty and connection.

Back home, curious to see if anyone had explored this comparison more formally, I turned to Google and a couple of generative AI tools. To my surprise, there wasn’t much literature explicitly connecting the two (though if anyone knows good resources, feel free to share). So I decided to lay out my thoughts and polish the ideas with the help of ChatGPT.

Let’s dive in.

The Courtship Phase: First Impressions and Chemistry

The early stages of both dating and dealmaking revolve around curiosity, subtle signals, and first impressions. Whether you’re meeting a potential partner or a potential client, both parties are quietly evaluating: “Do we click? Is this worth pursuing?”

From introductions and referrals to networking events and websites, the settings aren’t all that different. And from posture and tone to branding and pitch, how we show up matters. People decide quickly whether they feel intrigued, respected, or safe.

“You never get a second chance to make a first impression.” — Will Rogers*

There’s that familiar mix of optimism and skepticism, hopes and fear of rejection.

You don’t reveal everything up front—but you offer enough to suggest values, vision, and intent. If there’s chemistry—personal or professional—you move forward.

Mutual Discovery: Values, Red Flags, and Alignment

As things progress, you’re not just looking at surface compatibility anymore—you’re testing for alignment. Are we heading in the same direction? Do we share similar values, or at least understand and respect each other’s priorities? In both dating and dealmaking, this is where emotional intelligence matters most. Can you read between the lines? Can you spot red flags, but also give grace where it’s warranted? This phase is less about “selling” and more about “understanding.”

“Most people do not listen with the intent to understand; they listen with the intent to reply.” — Stephen R. Covey

We’ve all been on the receiving end of someone who talks too much and listens too little. It happens in meetings, and it definitely happens on dates. But when we take the time to really listen—not just hear, but understand—we open a door to real connection. It’s about genuinely understanding the other person’s needs, concerns, and motivations. That’s as powerful in a negotiation as it is in any conversation that matters.

Desperation Doesn’t Work: authenticity over performance

One of the more uncomfortable truths in both love and business is this: desperation rarely works. When we push too hard—whether to close a deal or keep someone interested—we often push people away instead.

“The best way to sell something: don’t sell anything. Earn the awareness, respect, and trust of those who might buy.” — Rand Fishkin

The key? Show up fully, but stay grounded. Confidence without attachment to the outcome is magnetic. Authenticity earns trust more than any polished pitch. In both worlds, people are drawn to those who are comfortable in their own skin—and clear about what they want.

Commitment: Defining the Relationship (or Deal)

Eventually, things get real. In dating, this is the “what are we?” moment. This is where you start expressing clearly your feelings. “Since we began talking, I’ve felt a spark of energy that’s hard to describe, and I can’t help but notice how naturally we connect and how good it feels when we’re together.” In business, it’s term sheets, timelines, and shared vision.

This is where clarity and boundaries matter most. Are you entering this deal (or relationship) because it truly aligns, or because you’re afraid to walk away?

“When you say yes to others, make sure you’re not saying no to yourself.” — Paulo Coelho

Saying “yes” to everything is easy—especially when we’re new or hungry. But real growth happens when we learn to say “no” when it matters. Whether it’s walking away from a mismatch in business or setting limits in a relationship, boundaries show clarity, not coldness. When we act from strength, we attract relationships (and deals) that are actually worth sustaining.

The Long-Term: Maintenance and Growth

And if all goes well? Whether it’s a relationship or a deal, the long-term work begins. Maintaining trust. Navigating changes. Communicating through friction. Reinventing when necessary. The best partnerships—romantic or professional—don’t just survive; they evolve. In this phase consistent effort is key to nurture a relationship and build a deeper connection. Sharing experiences and collaborating on meaningful projects together can bring you closer and strengthen your bond. 

When It Doesn’t Work Out: Ghosting, Breakups, and Moving On

Not every promising connection leads to a lasting relationship—or a successful deal. Sometimes it just fizzles. Other times, it crashes and burns. Either way, the experience can be surprisingly similar in both the romantic and business worlds.

Ghosting: When the Other Side Just Disappears

In dating, ghosting is when someone vanishes without explanation—no closure, no warning. In dealmaking, this happens more often than we like to admit. After a few promising emails, meetings, or even a verbal “yes, let’s do this,” the other party just goes silent. No returned calls. No updates. Just… nothing.

And you’re left wondering: Was it something I said? Did they find someone else? Should I follow up one more time or just let it go?

It’s frustrating, even disorienting. But it’s also a reminder that silence is, in itself, a signal. Whether in love or in business, sometimes the lack of communication tells you more than words ever could.

Breakups: When It’s Just Not the Right Fit

Other times, things fall apart more openly. Maybe after weeks (or months) of talking, it becomes clear that your visions don’t align. Or that trust has eroded. Or that one party wants to move faster—or slower—than the other. In dating, this is the “I don’t think we’re right for each other” talk. In business, it’s the “we’re going to pass on this opportunity.”

And while that can sting, there’s value in a clear “no.” It frees up both sides to move on, reflect, and—hopefully—approach the next opportunity with a bit more clarity and wisdom. 

It’s easy to take it personally, but often it’s just timing, fit, or evolution. Part of growing in either space is accepting when something has run its course—and learning how to let go with clarity and professionalism. Not every connection is meant to last. But each one can teach us something.

The Temptation to Force It

Sometimes, the hardest part is walking away when something almost works. Maybe the potential is there, but the timing is off. Or the values don’t quite line up. In both dating and deals, there’s a temptation to force it—to cling to the idea of what could be, even when the reality falls short.

But forcing a deal—or a relationship—rarely ends well. Eventually, cracks show. And what once seemed like a promising match starts to feel like a drain on your time, energy, or even integrity.

Hard to Get, but Worth Finding

Whether in love or in business, real connections and build something together is something we crave—but rarely get handed neatly. Sometimes we have to create it for ourselves. Reflecting on what went wrong (or right), writing down lessons, having one final honest conversation—if it’s possible.

Because in the end, every failed deal or broken connection isn’t just a loss. It’s a chapter. A learning moment. And in many cases, a necessary step toward finding something better aligned down the road.

And they lived happily ever after (well, kind of).

At its core, both dealmaking and dating revolve around the same fundamentals: emotional intelligence, self-awareness, and authenticity. They’re less about tactics and more about people—how we connect, communicate, and build trust.

“Business is ultimately about people and values.” — Howard Schultz

Success in either arena comes from understanding human behavior, managing expectations, and showing up with clarity and intention. When we approach business the way we approach meaningful relationships—present, curious, grounded, and real—we build partnerships that not only last, but thrive.

And when things don’t work out? We don’t just walk away—we grow. Every experience, whether a win or a miss, adds to our wisdom and resilience.

So yes, happily ever after is possible—professionally, personally, or both.
But let’s all agree on one thing:

Ghosting is never cool.