If you’re anything like me, you’ve made mistakes in dating. Big ones. The kind that haunt you during your morning shower and force you to audibly say, “Alright, let’s act like that never happened.” But the thing about mistakes is that they’re just fancy excuses to learn something the hard way. And boy, have I learned plenty.

Here’s the good news: you don’t have to make the same mistakes I did. I’ve been humbled by dating mishaps so you don’t have to be. From ghost stories (no, not the romantic kind) to relationship red flags so glaring they should’ve come with sirens, here are a few lessons I wish I knew earlier.

1. Be Yourself, But the Version That Actually Makes Plans

“Be yourself!” they say, as if that clears up everything. Look, I used to think that “being myself” meant winging date plans and impressing people with my spontaneous charm. Spoiler alert: that doesn’t work. For one thing, "spontaneous charm" only shines when you’re Cate Blanchett playing an art thief. For the rest of us, winging things just looks messy. And indecisive.

I learned this the hard way after telling someone, “Let’s do whatever feels right in the moment!” That moment ended with us eating gas station snacks in my car while she politely stared at the dashboard. She deserved better.

Lesson learned: Plan things. It doesn’t need to be a Michelin-star dinner or a grand-scaled picnic. A simple coffee spot that you like, a low-key museum, or even a walk along the lake (Chicago shoutout!) will do. It’ll show you’ve put in thought—which is basically flirting’s love language.

2. Don’t Ignore Red Flags (Yes, Even the Tiny Ones)

Have you ever pretended a red flag was “just pink”? I’ve been there too. The gym selfie “entrepreneur” who didn’t actually have a job. The person who always “forgot” their wallet. The “jokingly” sarcastic texts that felt like thinly veiled insults. I waved those red flags away because I wanted to believe people were better than they acted.

Here’s the thing: red flags don’t go away. They grow into full-blown banner parades. If something feels off—whether it’s a little nagging voice in your head or a friend pulling you aside to give you the look—listen to it. Your instincts aren’t trying to kill your vibe; they’re trying to save it.

Not every red flag means someone is bad, but it absolutely means they might not be good for you. Trust your gut.

3. Communication Actually Deserves That Much Hype

I hate to sound like your therapist (shoutout to mine, though), but communication is basically the cheat code to all relationships. I didn’t always know that. In my early twenties, I thought silence was a strategy. I’d just shove my feelings into my metaphorical closet and hope no one opened the door. Guess what? People do open the door—and then a bunch of unsaid emotions hit them in the face.

There was one breakup I should’ve seen coming because we both stopped talking about the things that mattered. We avoided conflict like Chicagoans avoid traffic after a Bulls game. But by not addressing the issue, we let it fester and become the very thing that ended us.

If something’s on your mind, say it—with care. Don’t make it weird, don’t wait for a dramatic moment, and certainly don’t let Netflix autoplay another episode while you sit in silence. Speaking up before problems pile up isn’t overkill—it’s mature.

4. “Cool” Is Overrated. Kindness Isn’t

Let’s talk about the myth of “cool.” You know, the too-casual, laid-back persona that never cares too much or tries too hard. For a while, I thought being “cool” would win people over. What that really meant was I wasn’t showing up as my full self.

One date called me out on this. I had tried to play it aloof, shrugging off compliments and making vague plans for a “sometime next week.” Finally, she straight-up asked, “Are you actually interested, or are we just passing the time?” She was right—I was interested. I was just too afraid to look uncool by admitting it.

Here’s what I know now: People don’t “fall for” cool. They fall for kindness, attentiveness, and the type of thoughtfulness that makes someone feel seen. Remember this: It’s cooler to care than it is to pretend not to.

5. Your Time Is Precious. Not Everyone Deserves It

Let’s put it plainly: some folks are just not worth your energy. I’m not saying this to be mean—I’m saying this because I’ve learned the difference between chasing potential and recognizing reality.

I once spent months pursuing someone who only gave me breadcrumbs of affection. They’d text every now and then, cancel plans last-minute, and only show up when they needed something but not when I did. I convinced myself that if I tried hard enough, it would work out. It didn’t, and I ended up frustrated, hurt, and with way too many sad playlists on repeat.

Here’s the truth: Love doesn’t require you to chase it down like it owes you money. Real connection? It meets you halfway. It values your time and returns your energy. You deserve someone who prioritizes you—not someone who keeps you as a backup plan.

6. Stop Comparing Your Story to Everybody Else’s

We live in the age of Instagram proposals and TikToks of couples rolling out matching pajamas. It’s easy to think, “Why isn’t my life that put together?” I’ve been there, torturing myself with social media highlight reels, wondering why my relationships didn’t look like those curated snapshots.

But then I remember: those highlight reels don’t show the full picture. They don’t show the arguments over whose turn it is to buy the toothpaste or the days when one person just needs space. Every relationship has its own pace, quirks, and challenges.

Your story is yours. It won’t always look like a rom-com or a Hallmark holiday special, and that’s okay. Love is custom-made. Let it unfold in ways that feel true to you—not Instagram-worthy.

7. Never Settle for Less Than You Deserve

I used to think settling was just something people did when they got tired of dating apps or long commutes to dinner dates. But settling happens in smaller ways, like ignoring your own needs just to keep someone around.

The day I stopped settling was the day things got better. I started asking myself, “Does this person actually align with what I want? Are they enriching my life—or just adding complications?” When the answer wasn’t clear, I stepped back. Scary, sure. But freeing.

Spoiler: This doesn’t mean you have to wait for perfection. It just means you have to wait for someone who grows with you, respects you, and maybe even pushes you to be a better version of yourself.

Growing Pains and Gains

Dating is rarely tidy. It’s a maze of awkward first encounters, glowing moments, and yes, even heartbreak. But every wrong turn is a step forward. The heartbreaks teach you what you truly want, the awkwardness builds resilience, and the mistakes? Well, those are part of the process, too.

Learn, grow, laugh at yourself when you need to (trust me, there will be moments). And always remember: You’re not alone in this. We’re all fumbling through the dance of connection together.

Just make sure you’re wearing your best metaphorical shoes while you do it.