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I took out the title of the series “From 29 to 31” like one of those sneaky Baptist churches that takes “Baptist” out of the name. For those of you who care about context… check it. For those of you who don’t, skip on down below these links.

From 29 to 31 (Volume 1: Machete Mandate)
From 29 to 31 (Volume 2: The Jug Landlord)
From 29 to 31 (Volume 3: CVS Romance)

Volume 4: Make Gatsby Great Again!

As late March/early April rolled around, I was sort of rolling along. I found myself on the verge of asking out another good friend, but, for reasons that aren’t for this blog, I didn’t. #PlotTwist

Then one night I found myself driving to another woman’s house for some food. I didn’t know what to expect.

She’d made some carnitas for some event and I jokingly asked if she’d save me some and she had. I’d been trying to get more/any real time with her, and was surprised that she was actually responding this way, but I still didn’t know…

Was I just gonna grab some food at the door and be on my way, or was this girl being pursuable? Was she kind of into me?

She invited in, I enjoyed dinner and several hours of great conversation.

This was a girl I’d asked out the previous year, but had turned me down because she had a boyfriend at the time…

Chill out…I didn’t know about him, so maybe I’m not too much of a homewrecker. (Although, I later was reminded that apparently I said, “Well…if that doesn’t work out let me know.”)


A few days later I found myself at her house again, and another great conversation ensued. This time I wanted to clarify. So I did and asked her on a date, and…

…she said “yes!”*



We went on the date, which was quite likely the most fun date I’ve ever been on.

Then we went on another… and another…

I was dating someone…Wait?! What?!


Yeah… it was the first time I’d been on anything past a first date in 5 years… and it was great!!


We ended up running into some things that didn’t go how either of us would have liked and we ended things.

As the spring faded away, after a little time and perspective, I realized, for my part of things, perhaps I had been narrow-sighted in my expectations and that I was willing to try again. 

I pursued her with a persistent hope that prompted her to say, “You remind me of Gatsby.”


I thought that whole Gatsby thing was a good thing.  Women like Gatsby right?

But in the end, she wasn’t having it, and it was a very unpleasant time for me as I failed to #MakeGatsbyGreatAgain.

In that process, I was hurt in some ways that I hadn’t been hurt in at least 5 years, some of which I’ve been able to share, some of which I held to myself, but that’s the cost of caring you know? 

I remember telling her early on, and I meant it, that I trusted her knowing that she would hurt me, not until she did. I want that to always be a hallmark of my care for people.

Pain is the tax of life.

 If you really want something in life, the tax will not be what stops you. It will however, if you let it, afford you the opportunity to forgo gratitude and enjoyment of what you have for a self-righteous and victim-hearted pity.

And so…I think that’s so much of what searching for love in relationships (and friendships in general) is about; trying to find who you will choose to pay that tax with and for, and who will pay it with and for you.

Admittedly, however, tax is less tolerable to pay when you’re not getting anything for it. It’s like an estate tax. You’re just paying because someone or something died. That’s a double whammy, and that’s what I was left paying.

So why pay it?

I chose to pay it for the unseen, not the seen. 

I knew whether or not this was the woman I’d spend my life with, I’d need to continue my habit of facing pain head on for sake of those who may look to follow me later in life.

Pain evasion is not a legitimate option, because I don’t want those I care about caught up in my back taxes later in life. As such, I needed to exercise the muscles of a resilient hope by wading through some difficult, yet empowering revelations.

Ya see… this was my first chance to work through a relationship with the understanding gained from 5 years of traveling the world and leading others in their spiritual journey.

I was 5 years older than my last relationship, 8 years older than the one before that. I’d been able to look back on my past decisions and pull some wisdom from them, which is good, but insufficient.

I’d come to believe the next time I dated someone would be “her.” 

Gone was the young foolish man of my early and mid-20s. I would patiently choose well. If anyone would put up with me enough to date me they’d stick, and… if I started to give my heart to someone ever again, if anyone ever actually were able to pull my affections and attention from the sea of the wonderful women in my life, she would almost assuredly be “THE ONE”

I’d made the mistake, perhaps, of overvaluing the lessons learned as a way to shield myself from remnant grief.

Yeah… I’d experienced pain and made mistakes, but THE next woman I dated was going to reap a lifetime benefits from the character built those failures turned into lessons. 

But what happened when I couldn’t salvage our dating relationship with a Gatsby-sized hope?

I felt like a fool all over again, and because I’d found so much of my identity and worth in my perspective and wisdom, the sting was deeper. 

I think we idolize growth. 

We wanna grow, which is good, but we forget that, with the death of His son Jesus, God said we were enough before we ever grew at all. 

We idolize growth and wisdom, when they will not inherently satisfy in the face of brokenness. 

Wisdom didn’t care about me.
Wisdom wasn’t gonna hold my hand. #PhysicalTouch(that’s for you Josh Beebe HA!)
Wisdom didn’t die for me.

So I sat with fresh pain, to seek the Lord and not wisdom. In that time I found Him and more of His sufficiency, and ultimately, some more understanding of myself on top of it.

I came to realize that I’d held a couple of deep-seeded desires that had become entitlements unknowingly.

1.  That she (or anyone) would want to fully understand me

2.  That she (or anyone) possibly could fully understand me

Though I deeply want those things to be true of a woman, the chances of that happening aren’t “massive,” and my entitlement to those desires is even less. In actuality, if we end up with anyone, even they won’t be able to fulfill those expectations, nor us for them.

As a result, though I still had pain and hope, I was able to release her from being ensnared in the prison of my hurt, because she’d not robbed me of anything I deserved, but merely what I longed for at most. I still had hurt, but the Lord was the one stewarding it.

As summer wound down, something inside me subconsciously must have believed…


 So how did that turn out?
Check back soon to find out… if ya want.


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