You’ve been on a few dates, and something’s just not clicking. You’re bringing your best self (or so you think), but you still can’t seem to get past the first or second date. Cue the terrible chick flicks (Christmas Prince, anyone?) and mint chocolate chip ice cream (yes, it’s still the best flavor).
Hate to break it to you, but... sometimes you are the problem.

Let’s talk about the most common bad dating habits—and how to kick them to the curb so you can finally find a relationship that sticks.

🚩 1. Being Too Available

I know you’re excited—he’s hot, you’re vibing, and he finally asked you out. But showing up the second he calls doesn’t leave room for anticipation. And yes, the chase matters.

Try this instead: If he asks to hang out on Friday, say, “I actually have something going on—how about Saturday?”
Now you’re showing that you have a life outside of dating, and that makes you way more appealing.

🚩 2. Not Acting Like You’re Girlfriend Material

Let me explain. If you’re known as the party girl, your place is a hot mess, and you curse like a sailor 24/7… it might be time for a little self-check.
Dating is kind of like an interview—you don’t want to fake it, but you should still put your best foot forward.

Funny story: The Comedian was never on time, but on our first few dates, he made a huge effort to be punctual because he knew I valued it. His mom later revealed his lateness was legendary—I had been bamboozled. But by then, I was in too deep. 😅

Moral of the story? Be the person you want to attract before getting into a relationship.

🚩 3. Being Too Picky

I’m all for having standards, but if you’re holding out for a Christian Grey fantasy, you might be waiting a while.

Make a list of your top 5 non-negotiables. These are the “must-haves” that truly matter to you—values, goals, lifestyle, etc. The rest? Let it go.
Need help? Download my [Dating Terms worksheet] to narrow it down.

🚩 4. Flakiness

This one’s a dealbreaker. Integrity matters. If you say you’re going to show up—show up. If something comes up, just send a quick text. It literally takes five seconds to say, “Hey, I’ve had a rough day. Can we reschedule?”

People remember how you treat their time. Flakiness is a red flag you’re not emotionally ready to date.
(If you're curious, I once dated a notorious flake. The full story’s here → link it up!)

🚩 5. Ignoring Your Insecurities

This one’s big. If you haven’t dealt with your insecurities—abandonment, body image, past trauma—they’ll creep into your dating life.

I’ve been there. I used to lie about my past and apologize constantly because I was insecure. You don’t have to carry shame for things that shaped you.

Do the work. Therapy, journaling, books—whatever helps you heal. Because when you love yourself, you stop choosing people who don’t.

💡 Final Thought

Dating isn’t just about meeting the right person. It’s about becoming someone who’s ready to receive love when it comes. When you’re grounded, self-aware, and committed to your own happiness, the right relationship shows up like magic.

Now go finish that ice cream and start fresh.

I’m not sure if this phrase has been officially coined, but a close friend and I use the term “Ugly Duckling Syndrome” to describe people who are attractive, smart, witty—and still suspiciously insecure.

They often grew up shy, awkward, overlooked, or in the shadow of a sibling who got all the praise. And while the glow-up may have come later in life, the emotional scars stuck around.

I didn’t realize how much this applied to me until a friend pointed it out. I tend to be unaware when someone is interested in me, and I often don’t recognize that I might be attractive in certain settings. Thankfully, I have amazing friends who lovingly slap some sense into me when I need it.

Dating With Ugly Duckling Syndrome

As I’ve dated older men, I’ve noticed this is something they pick up on quickly. Maybe it's because I spent years dating mimbos (you know the type—gorgeous, clueless, emotionally unavailable), and never had to face the full reality of being seen.

The thing about dating someone with Ugly Duckling Syndrome?
They’ll often deflect compliments, minimize their achievements, and joke away any attention.

My close friend—who I lovingly call my dating guru—once told me:

“Two Ugly Ducklings should never date. You need someone who sees you—even when you don’t see yourself—and pulls you up, not down.”

That hit me.

I’m confident in my career, my wit, my mind. But when it comes to physical confidence? I can be blind. And I’ve dated others who’ve been the same.

Case in Point:

I once dated a local amateur comedian—funny, charming, kind, and completely oblivious to the fact that women were clearly hitting on him after his sets.

He’d walk off stage, and I’d say, “You realize she was flirting, right?”
And he’d look at me blankly.

Don’t you know the best way into a woman’s heart (and maybe her pants) is to make her laugh?

Still, I loved watching him get attention.
It secretly boosted my ego.

“He’s going home with me,” I’d think, proudly.

But over time, I focused so much on propping him up, I stopped seeing red flags.
I lost myself.
The relationship became emotional—and exhausting.
And that’s another insecurity I’ll unpack in a future post.

It’s Not Just Me

I have a close friend who’s beautiful now—but she used to weigh 230 pounds in high school. She’s near 130 now, stunning, and still worries constantly about her weight.

Sometimes I just want to shake her and say:

“Look at what you’ve accomplished. Two kids, a full transformation, and you still look amazing. Be proud. Now get dressed—we’re going out.”

So If You Know Someone With Ugly Duckling Syndrome…

Don’t get frustrated. Just be present.
Sometimes all they need is someone to remind them who they are—until they finally see it for themselves.

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Bad Dating Habits and How to Fix Them