Lessons in Dating


I’ll be turning 26 this week, and there’s plenty of life reflections to be had. But as a true testament of growth and progress, it’s worth noting the lessons learned from dating.

Getting dates (or even just getting close to almost having dates) is an awesome rush of a feeling. But for most of my life I couldn’t process it that way. Before, I would never imagine myself being able to take my misadventures in stride.

I was way too busy being a wreck and saying some really, really emo stuff.

“… maybe my soul mate’s already dead.”

I was all serious business, and I didn’t know how to stop. I didn’t know how to crack the code. I never felt like I knew what signs to look for.

So looking back, I’d tell my old self…

1. Chemistry is Wack


Having chemistry is totally overrated. Sure, you want compatibility, but avoiding incompatibility is too basic to have substantial meaning. I get it: “falling” for someone feels great, but that wave of emotion has got to be the most inaccurate way to gauge compatibility. You want someone to sweep you off your feet or floor you? Join a martial arts class!

I’ll admit, you can’t always keep your guard up in this area. You just need to be realistic and acknowledge that several things can set you up for feeling this false sense of love–drunkenness, loneliness, horniness, and any combination of the three.

And if you’re hit with that, it’s not that you can’t have a good time. Just understand that isn’t love. That’s infatuation. You don’t really know that person.

Even if you do get to know someone and build rapport, realize there’s different types of chemistry. Getting along and enjoying each other’s company? That’s how you make legit friends. Those can be solid relationships without exclusively being linked to romance.

The bottom line: you can enjoy the butterflies, but you shouldn’t always trust the butterflies.

2. Don’t Look for Signs


I can’t say outright that signs don’t exist because they… might?

But if you have trouble navigating your confidence and insecurity like I did, it’s likely that you’re going to misread a lot of stuff. You’ll either spin every chat and text into nauseating optimism (she totally wants me) or pitiful pessimism (she didn’t pick up? she hates me).

If you fall into the latter category, you waste a bunch of time agonizing over BS you don’t even know is real. It becomes way too easy to get caught up in the melodrama of a conversation taking place in your head.

You have to keep things grounded in a real conversation.

3. Always Ask!

Getting rejected sucks. But wondering what could’ve been is worse on the psyche. Go hang out with your person of interest and get some closure!

What if I… Maybe I should’ve…

— I’m sure all my friends could’ve done without all the whining.

And just so we’re clear: it’s not only a matter of asking someone out to coffee, lunch, or dinner. I know working up the nerve to be up front can take a lot of energy for some. But, please, please, please, do yourself a favor and confirm if this person is even “available” in the first place.

Otherwise, you might be spending all your dough on a girl who’s seeing someone. Being taken might not bother some people I guess, but it’s good to know what you’re getting yourself into.

4. Never Beg

Wanting a relationship ain’t a bad thing. Going into each episode with enthusiasm is good! But being over-eager… that’s really no different from being desperate.

You can try to highlight your good side, but this isn’t a business. Sweating over the right answers, the right timing. You shouldn’t have to be making a sales pitch.

Relationships take work, but not this kind of work.

“But I could be so good for you!”

Is it worth it to be in a relationship where you had to persuade the person to be with you? Is it worth it to be in a relationship where you had to convince them of what you could do for them?

People are free to choose. Sometimes they get it right. Sometimes they get it wrong. Have some pride to say, “Oh well, their loss” if you don’t get picked.

Handling yourself with that sort of dignity will require a certain amount of self-esteem.

5. Friend Zone Yourself

No, I’m not telling you to brace yourself for rejection early on. I’m talking about how you shouldn’t buy into all this mainstream portrayal of love.

Don’t believe the hype that dictates you’re incomplete.

You have to know you already have what you need most: yourself. For everyone who reads that as a profound epiphany, I’m sure there’s much more people groaning and rolling your eyes. I promise it’s not supposed to be some shallow optimism.

It’s a reminder: you’re always got yourself in your corner. And so, you got to be your biggest fan. A fan that appreciates you. A fan that’s always there to support you.

If you’re not happy with yourself, having a relationship doesn’t fix that. Self-loathing will still lie underneath.

You know how true friends don’t give a shit when you slip up here and there? True friends don’t lie in wait hoping for you to mess up? Can you do the same for yourself?

When you friend zone yourself– when you’re able to give yourself the kindness that you keep looking to get from others– you will get peace of mind. Give yourself a breather.


Published by Jon Dao

Formerly, the Conversation Coach

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