5 Reasons to Stop Being “Cool” on Dates

Malinda Fusco


Photo by LIGHTFIELD STUDIOS on Adobe Stock

It’s natural to try to impress your dates. But trying to be “cool” is a common dating faux pas.

It’s also one of the worst you can make. I should know — I made it a lot during my early dating days. To my eternal embarrassment, one would-be boyfriend called me out on it.

After a few dates, he half-jokingly said, “I thought you were cool.”


I just fooled him into thinking I was cool and there I was…unable to hide my lack of coolness and, therefore, our lack of compatibility. 

At least, that’s what I thought at the time. It took me a while to realize that trying to be cool while dating is actually the biggest self-sabotaging move you can make.

After that very awkward exchange (and the decision to not keep seeing each other, surprise surprise), I realized faking coolness is overrated.

In fact, trying to be cool on dates is a great way to sabotage any potential romance. Here’s how it can backfire.

1. They won’t like you for you.

This is obvious, right? Yet, so many people are willing to portray themselves as something else in order to impress others, whether it’s colleagues, friends, or potential partners.

If you’re successful in faking them out, then you’re not really successful. Sure, they might like the front you portrayed, but do they really like you?

And now, you have to maintain the lie. You have to keep the “cool” act going, otherwise you risk them telling you things like, “I thought you were cool.” Eek!

Maintaining appearances for things like work and professionalism is hard enough. If you have to maintain appearances in your relationship, you just turned your relationship into a job. Yeah, not fun.

2. You’re wasting both of your time.

All of that time that you could have been assessing if you two are compatible is wasted.

Dating is typically used as a time to see if you’re going to click as a couple. When you fake your coolness, you’re wasting not only your time, but their’s too.

You’re giving them false information to make judgments with, which will lead to faulty decisions.

And when it all falls apart? Well, you’re back to square one. That time you spent faking it? You still need to spend it, and it would be better spent with authenticity to see if you’re compatible.

3. You could both be faking.

Maybe you’re both faking it because you like each other so much. Well, that’s even worse.

Let’s say you’re ashamed of your massive anime addiction and you don’t mention it. What if your love interest also likes anime? What if they don’t mention it because they’re ashamed too?

If you just wait to see if the other person will mention it first, you may never find those connections. Or you could end up in a relationship where it takes a long time to realize you both like the same thing.

The best-case scenario is that down the road someone slips and mentions it, and you suddenly realize you have a common interest. You could have had that from the start.

4. You’re probably dating for the wrong reasons.

If you’re trying to hide who you really are, are you really dating for the right reasons?

You need to evaluate why you like this person so much that you feel the need to be something else. Chances are, the reasons you like them are shallow — like they’re super hot! Been there, done that. It’s a valid enough reason for someone to catch your eye, but relationships need to be more than physical attraction.

You could be dating someone based on the same interests, desires, and life goals. That’s what will keep you together for years to come. Physical beauty fades.

5. They think you’re boring, so they break up with you.

Trying to be cool can backfire. Horribly. You could be trying so hard to please them and adjust to their interests that they find you boring.

The kicker is that if you’d been yourself, they would have actually thought you were cool. When people are passionate about something, they light up in a way that can’t be faked. That is true beauty and attraction can easily stem from that.

You deserve someone who will watch you light up about some weird shit you like and smile too.

The Takeaway

It was once I embraced my own version of “cool” that I was able to find my boyfriend. We’ve been together for years, and he finds me cool (sometimes). But I don’t have to try so hard for it. And I can be my nerdy, weird self without judgment.

Trying to be “cool” undermines the entire dating process. Be yourself and you will find someone who thinks you’re cool without trying. You won’t have to put energy and effort into being what you aren’t.

Only then can you build a relationship based on authenticity and true connection.

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