It wasn’t even February yet. 

It was the end of January, and Kenzie and I were doing a quick Target run after media class. I mean, nothing is a quick Target run—you go for one thing and come back with 10. 

But our not-so-quick mission took us right past the display. You know the one. Deep red hearts and cute couple catchphrases in silky, sparkling cursive. 

“Oh no—it’s Valentine’s Day,” I rolled my eyes.

I was about to launch into my bitter diatribe about how I avoid social media for three days before and after Valentine’s Day because, being single for -th time in a row, I don’t need to be reminded of what I still don’t have. 

But Kenzie totally ruined it. 

“Valentine’s Day is one of my favorite holidays!” 

I glanced at her, as single as me, also in her late twenties—and wondered if she was serious. But her eyes were sparkling. 

“There’s always hope,” she smiled.

Usually that’s my line. But that day, she stopped me in my tracks. 

It was time for me to rethink being single on Valentine’s Day. 


Three years ago, I wrote a blog post about being single on Valentine’s Day. I talked about how “being content” isn’t the goal. Loving Jesus is. Which means we need to be honest with him, even when we’re not content. Even when we’re hurting. He’s there. 

But fast forward three years, you found me in Target still triggered by flower displays. Great. 

Except Kenzie’s declaration—there’s always hope—had already started to set things in motion.

The following week, I was at our women’s fitness class. Our coaches often pray to start and share a theme or word for that particular day. Usually I’m all in, but when Natalie said “freedom”, I wasn’t particularly moved. Oh, no problem, it’s for somebody else.

So I got caught up in the group workout with Ali and Reisa, rotating through burpees, box step-ups, and the row machine. I was nailing it. I was great. I had my rhythm. 

But in the middle of it all, Natalie shouted, “Don’t forget to ask Jesus what he wants to give you freedom from!”

With no warming, it instantly came to mind: 


My box step-up pace was ruined. I could barely hold up the one dumbbell. Not without choking up, anyway. Why?

I knew it was true.


Before I go on—I need to tell you I am a firm believer in grieving well. Often well-meaning people are too quick to dish out “don’t feel sorry for yourself” when you really just need someone to hand you tissues. 

And as a recovering over-optimist, it took me awhile to learn that Jesus wanted to sit with me in my pain, and not rush me out of it. Blessed are those who mourn (Matthew 5:4), remember?

So whenever I hear people use phrases like “just leave your emotions at the door” or “just praise God and ignore how you feel”—I have an allergic reaction. We can’t afford to forget that Jesus is “well-acquainted with grief” (Isaiah 53:3). 

So, I got through the rest of my weighted box step-ups and told God: We’re talking about this later. 

We did, walking around campus the next day. I wanted to know the difference between getting free from self-pity—and denying pain He wanted to heal. 

I was surprised with how quick and clear the answer was. 

Kayla, self-pity is about how you want others to treat you.
Grief is about being honest with me about the pain you feel. 

I was stopped in my tracks. Well, not actually. I was walking to the mailroom and didn’t actually stop my steps. 

But it all made sense. 

In the last month, I had started to slip into this mindset: I wanted people to feel sorry for me. I wanted everyone to know the pain I was feeling. You know, single and 29 with all siblings married—not to mention the behind-the-scenes drama that deserves a chat over a cup of tea.


The lure of people feeling sorry for me—oh, it was much more attractive than facing my reality.

One, that I was hurting (therefore I needed to grieve what hasn’t happened). 

Two, that I was doing much better than I thought I should be. Being single wasn’t actually the worst thing in the world, and I was moving forward in my dreams to write and illustrate children’s books—and my dreams of traveling the world telling stories of what God has done. 

Self-pity was clawing at me, trying to get me to disregard how happy I actually was. 

Or should I say, how happy I actually am

Because this brings us to the present, only a few days shy of Valentine’s Day.

I live in Hawaii (never expected I’d do that again, let alone love it) and work with an incredible team, I live in a lovely home near my family and drive a lime-green car that always reminds me that provision can be more vibrant than we expect. 

I could dread Valentine’s Day again, if I wanted to. 

I could write a grand history of disappointment. I could make myself cry.

But instead, I walk through Target and my eyes sparkle. 

I actually smile at the deep red hearts and cute couple catchphrases in silky, sparkling cursive. 

Now, it reminds me: I am already loved. 

So, my self-pity got ambushed. 

Because: there’s always hope.

And Valentine’s Day might not be that bad after all.

Photos: Fabrique Bakery, Notting Hill, England. April 2019.