Picture this: You’re on a discovery call, and the rep launches into rapid-fire questions without any context. “What’s your budget? Who’s the decision maker? When do you need this implemented?” Meanwhile, you’re thinking about the actual problem you’re trying to solve, but they’re already three questions ahead, scribbling notes like they’re filling out a form.
It’s exactly like being on a date with someone who asks about your salary, relationship history, and whether you want kids before you’ve even ordered drinks.
Here’s what’s fascinating: this parallel isn’t just amusing. It reveals something fundamental about why traditional sales approaches fail so spectacularly.
The Desperation Problem
I once watched a rep lose a six-figure deal in the first ten minutes by asking, “So what’s stopping you from signing today?” The prospect had called to learn about the product. The rep heard “interested buyer” and immediately started closing. It was painful to watch—like witnessing someone propose at a coffee shop meet-and-greet.
Both behaviors stem from the same place: scarcity thinking. When you believe this might be your only shot, you try to extract maximum information as quickly as possible. But desperation is repulsive in any context.
Great salespeople, like great conversationalists, operate from abundance. They’re genuinely curious rather than frantically collecting data points. They ask follow-up questions because they care about the answers, not because they’re checking boxes on a qualification framework.
The Authenticity Trap
Here’s where the dating analogy gets really interesting. We’ve all met someone who was clearly performing a version of themselves—saying what they thought we wanted to hear, mirroring our interests, presenting a carefully curated personality.
Sales training often teaches the same thing: match and mirror, find common ground, build rapport through superficial connections. But just like in dating, people can sense when you’re performing. It creates an uncanny valley effect—something feels off, even if they can’t articulate what.
Think about the rep who suddenly becomes a sports fan when they notice your team’s logo, or starts using industry jargon they clearly don’t understand. Compare that to the rep who says, “I don’t know much about manufacturing, but I’m curious how this process works for you.” Which one would you trust?
The alternative isn’t being authentic (whatever that means). It’s being consistent. Show up the same way in every interaction. Let your actual personality—flaws and all—be part of how you do business.
The Patience Paradox
Traditional sales wisdom says always be closing. Traditional dating wisdom says... well, something similar. Both approaches miss the point entirely.
The best relationships—romantic or professional—develop at their natural pace. Trying to accelerate intimacy (or commitment) usually backfires. But so does endless circling without ever making a move.
I know a rep who spent eight months “nurturing” a prospect who was never going to buy. Meanwhile, another rep lost a hot lead by pushing for a contract signature after a single demo. Both failed for the same reason: they weren’t reading the room.
The skill isn’t knowing when to close. It’s reading the situation accurately enough to know when someone is ready for the next step. This requires actual attention to the other person rather than focus on your own agenda.
What This Really Reveals
The sales-dating parallel isn’t just cute—it exposes why so much sales advice misses the mark. We treat sales like it’s about persuasion techniques and process optimization when it’s actually about human connection and mutual evaluation.
Both sales and dating are fundamentally about two parties trying to determine if there’s a good fit. When one person is focused on “winning” rather than genuinely evaluating compatibility, the whole dynamic becomes manipulative.
The best salespeople, like the best partners, are equally invested in finding out if this is right for both parties. They’re willing to walk away from bad fits because they understand that forced relationships never work long-term.
The Real Lesson
Stop trying to be impressive. Start being useful. Stop trying to control the process. Start paying attention to what’s actually happening.
Whether you’re selling software or looking for love, the fundamentals remain the same: show up consistently, listen more than you talk, and remember that the other person’s experience matters as much as your own goals.
The irony is that once you stop trying so hard to “win” the conversation, you start having better conversations. Better conversations lead to better relationships. Better relationships lead to better outcomes—in sales and everywhere else.
Everything else is just technique. But good technique without genuine interest in the other person is just sophisticated manipulation. And everyone can sense the difference.