Why Does It Matter? A Reflection on Love, Ego, and Insecurity

Being in a relationship like the one I’m in now has opened my mind to things I would have never explored while single. It’s such a strange feeling. When I was single, if a guy dismissed me, my ego would kick in and I’d think, “He has no idea what he’s missing.” I knew what I brought to the table—smart, funny, independent, confident. Why wouldn’t someone want that?

But now that I’m in an amazing relationship, my insecurities have started to bubble up in ways they never did before. When you’re single, it’s easy to brush things off because there’s always another adventure, another guy, another distraction. But in a committed relationship—when everything is going great—that’s when the deeper questions creep in: Is it enough? Am I enough?

The truth is, of course it’s enough. He’s with you because you’re worthy. You always were.

I talk to friends all the time about their insecurities. When I’m on the outside looking in, I find myself asking, Why does it matter? So what if he hasn’t answered your text or liked your post within seconds? He might be busy. If at the end of the day he’s showing up, being present, and making you feel loved—that’s what matters. But I get it. In relationships, especially for fiercely independent women, vulnerability can feel foreign—even uncomfortable.

When you’ve been relying on yourself for everything—your time, your space, your energy—sharing your world with someone else can be hard. And letting go of control? Even harder.

Last week, I had a vulnerable moment that challenged me deeply. I’m a perfectionist, and when I feel like I’m not “perfect,” it bruises my ego. Looking at yourself honestly is tough. It’s easier to give advice to someone else than to deal with your own emotions and sit in the discomfort.

Luckily, my boyfriend and I made the decision early on to keep God at the center of our relationship. And not to preach, but that decision grounds me. When I remember that I am already perfect as God intended me to be, it becomes easier to embrace love, flaws and all. During that moment of doubt, I realized it was my ego getting in the way. A distraction. A tactic to distort what’s real. Love is meant to be joyful. Don’t let negativity, insecurity, or pride cloud your view.

I once heard a comedian joke, “If anyone ruins a relationship, it’s the woman.” I hate that stereotype—but I understand where it comes from. Sometimes, women overthink things because we crave connection and clarity, while men operate with simple intentions. If they want you, they’ll make it clear. They won’t play games.

So when you catch yourself spiraling—second-guessing, analyzing, overreacting—stop and ask: Why does it matter? If the love is real and you’re both showing up for each other, trust it. Trust Him. Trust you.

Ugly Duckling Syndrome: Insecurity That Outlasts the Glow-Up

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.