Quick Judgment: The Biggest Mistake People Make In Dating

You know the scene: you unlock your phone, skim one line of someone’s bio—“loves karaoke”—and instantly swipe left. That lightning-fast verdict trips up even the smartest singles. So let’s talk about the number one mistake people make in dating—the one that sneaks into nearly every modern dating story: quick judgment. One glance at a photo. One line in a profile. One “meh” conversation. And poof, we write someone off before we even know who they are.

This mistake people make in dating can cost you a real connection

As a professional matchmaker and dating coach in Boston, I see it every day: we glance, we judge, and we move on. We tell ourselves stories like, “If he’s 5'9", he must be shorter in person,” or “She’s holding a cat—she’ll never travel.” Boom, potential partner deleted.

We make wild stories about people based on minimal information. A guy says he loves comic books - suddenly, he’s “immature.” A woman mentions she’s spiritual, and someone assumes she’s all crystals and moon circles (nothing wrong with that, by the way).

In my experience as a matchmaker in Boston, this snap judgment habit is the biggest mistake people make in dating, and it's blocking more real connections than you think.

Expecting instant chemistry, instant clarity, instant everything is one of the most dangerous traps for modern singles. And honestly, it’s not your fault. We live in a culture that’s obsessed with convenience. Everything in our lives is built for speed: groceries delivered in under an hour, entertainment on demand, packages at your door tomorrow. So, of course, it feels natural to expect dating to work the same way. You swipe, you match, you meet, and BAM... fireworks.

But a real connection doesn’t work on Prime shipping.

Deep attraction, emotional safety, trust, and compatibility take time to reveal themselves. Chemistry isn’t always obvious in the first five minutes. In fact, it often starts with comfort, not lightning. You may not get butterflies. You might just feel... calm, curious, intrigued. And that? That’s more valuable than you think.

As a dating consultant, I’ve worked with clients who nearly skipped their now-partner because the first date was “just okay.” One woman told me, “I wasn’t sure if I felt that spark.” Three dates later, she was laughing her way through dinner with someone who had become her safe place. She just needed time to see him, not judge him.

If you’re swiping for instant magic, you might be missing the people who are truly right for you, because most great relationships don’t start with fire. They start with a flicker. And only the people who stay present long enough get to see it turn into something lasting.

So if you’re looking for real love—not just entertainment—drop the Amazon Prime mindset. Love isn’t a product. It’s a slow-build connection between two humans with messy, beautiful layers. And that kind of love doesn’t show up on demand. It shows up when you stay.

Fun fact: On a podcast, The Diary of a CEO, Michelle Obama shared that Barack did not check her "boxes" and she rejected him first. She even tried to introduce him to one of her friends. 

How to break the habit of quick judgment and not repeat the biggest mistake people make in dating

If you want to stop making the biggest mistake people make in dating, here’s how to shift:

1. Give it a second look. Before you dismiss someone, reread their profile. Look for one thing you’re curious about. Curiosity is way more useful than critique.

2. Try to ask better questions. “What do you do for fun?” is fine. But try, “What’s something that made you laugh this week?” or “What’s your dream weekend?” Get beyond the basics.

3. Get off the app faster. You’re not going to bond through an endless text thread. Suggest a phone call or a quick coffee. Real humans are always more layered than their profiles.

4. Expect real, not perfect. If you expect instant fireworks or a soulmate checklist, you’ll miss out. Some of the best relationships start slowly, so don’t confuse “not blown away” with “not worth exploring.”

5. Notice your narrative. Are you telling yourself, “This will never work because…”? Ask instead: "Is that actually true, or is it just fear talking?".

Now you know how to avoid the biggest mistake people make in dating

If you’re serious about finding love, you’ve got to play a different game than the one apps teach you. You have to show up with patience, curiosity, and a little courage. That means ditching the fantasy of the “perfect” profile and learning how to actually connect.

Any dating expert will tell you: The most common mistake people make in dating isn’t swiping the wrong way or saying the wrong thing. It’s not taking the time to really see someone. And honestly? That’s the same mistake that leaves so many people still single, not because they’re unlovable, but because they never gave connection a real chance to grow.

The real magic in dating doesn’t happen in the first five seconds. It happens when you’re still willing to sit across from someone after five dates, still discovering who they are.

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Anna Morgan Coaching specializes in guiding men and women in breaking through emotional barriers and developing the mindset and skills needed for successful dating. Anna offers 1:1 dating coaching for men, dating coaching for women, matchmaking, relationship coaching, and empowering dating profile pictures for successful online dating. Book a free discovery call and learn how your dating life can be changed.