When Good On Paper Feels Empty Inside

You’ve done everything right. You’ve clarified your values, opened your heart to new possibilities, and even followed the three-date rule. But there you are, sitting across from someone who checks all the boxes while your heart whispers “meh.”

This week’s Dear Damona question comes from Taylor who’s wrestling with a frustration that hits so many intentional daters:

“I recently met a decent man who broadly matched my goals and values, was a good communicator, reliable, etc. I went on three dates, but each time I felt like I was dragging myself. I wasn’t excited to be with him, but I pushed through because I remembered your advice on giving it three dates when there’s no chemistry to see if it will build. Upon reflection, I’ve realized sense of humor is really important to me. If a man can’t make me laugh or at least find my jokes funny, I struggle to feel a connection. But I’m worried that I’m letting decent men slip by just because they’re not funny.”

Sound familiar? Let’s talk about what happens when compatibility meets reality, and why trusting your gut doesn’t make you too picky.

(00:05:00) The Three-Date Rule Has One Big Caveat You Might Be Missing

Here’s what most people get wrong about the three-date rule: it’s not about grinding through three painful encounters because someone told you to. The magic word here is CURIOUSITY.

If you’re feeling dread about seeing someone again, if you’re checking the clock during dinner, if you feel depleted rather than energized after spending time together, you already have your answer. 

“The three-date rule is if you are not curious about them after the third date, and you’ve given it those three dates to not only get to know them, but to also open up yourself,” Damona explains.

Because here’s the thing: you might not be fully yourself on date one either.

The rule exists to give both people space to get comfortable and reveal who they actually are. It’s not a prison sentence that forces you to power through misery in the name of being “open-minded.”

(00:14:00) Your Body Knows Before Your Brain Catches Up

Want a foolproof way to gauge connection? Do an energy check the moment each date ends. Not tomorrow, not when you get home and overthink it. Right when you get in your car or step onto the train.

Ask yourself: Do I feel more open or more closed after spending time with this person? Am I energized or completely drained? Your immediate physical response will tell you everything you need to know about compatibility.

This is exactly why our free Date Tracker tool includes space to capture these energy shifts while they’re fresh, so you can spot patterns about what types of people actually enhance your life.

Just make sure you’re not in a season of general malaise that might be clouding your judgment. If you’re feeling “blah” about work, friends, and everything else in your life, you might need a dating pause rather than a new person to fix your energy.

(00:16:00) Why Humor Isn’t Shallow (It’s Actually Genius)

Before you feel guilty about wanting someone who makes you laugh, understand what humor really reveals. 

It’s not just about entertainment. It’s a sophisticated compatibility test that shortcuts months of getting-to-know-you conversations.

Shared humor signals shared experiences, cultural understanding, and similar worldviews. When someone gets your joke, they’re showing you they speak your language on multiple levels. When they don’t, you’re discovering a fundamental disconnect.

“Humor actually demonstrates some other things that are really important in compatibility,” Damona notes. “Humor is a sign of shared experience. One of the reasons that you don’t find someone’s humor funny is because you might not be able to relate to it.”

But here’s where it gets deeper: humor is one of the few ways we show bravery in everyday life. When you tell a joke, you’re taking a social risk. When someone doesn’t acknowledge that risk or meet you where you are, it leaves you feeling exposed and disconnected.

(00:22:00) Decent Is the Bare Minimum, Not the Goal

Let’s address the guilt you’re carrying about “letting decent men slip by.” Here’s your reality check: everyone should be decent. 

Kindness, reliability, and basic communication skills aren’t special qualities that deserve a gold star. They’re the cost of entry.

You’re not being too picky when you want more than the basics. You’re recognizing that you deserve the extras, the upgrades, the things that make someone not just a match, but a match for you.

Stop normalizing decency as something to be grateful for. Start expecting it as the foundation upon which everything else gets built. The chemistry, the humor, the intellectual connection, the way they make you feel seen and understood. Those aren’t bonuses. Those are the real relationship goals.

(00:25:00) Why You Can’t Pre-Screen for Chemistry (And Should Stop Trying)

Stop trying to assess compatibility through texts, dating profiles, or even FaceTime calls. You cannot accurately judge someone’s humor, conversational skills, or chemistry until you’re face-to-face.

• That hilarious texter who goes silent in person? 
• The witty profile writer who can’t think on their feet during dinner? 
• The charming phone conversationalist who has zero physical presence? 

You’ve probably met them all.

So save yourself the false hope and get to the in-person meeting as quickly as possible. Match, maybe do one screening call, then meet within a week. Everything else is just delayed disappointment.

Trust the process: goals and values can be discussed on paper (or on screen), but to get to the other pillars of long-term compatibility from F the Fairy Tale, you have to feel someone out. And when it doesn’t feel right, don’t override your intuition with logic. Your body is giving you information that your brain can’t argue with.

💌 Have a relationship question that’s been weighing on you?

From dating dilemmas to family dynamics, friend boundaries to figuring out the right response to that confusing text, Damona wants to hear it all.

Send your question in a DM or voice memo on  Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

Remember: Dates & Mates covers every relationship that shapes your world. Romantic partners, friendships, family connections, and most importantly, your relationship with yourself.

📝 Want to keep track of what’s working (and what’s not) in your love life?

Get your free Date Tracker at damonahoffman.com/datetracker

📖 Get a copy of Damona’s book to learn more about the Three Date Rule and how to find love successfully:

“F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”