GROWING UP JASON ~ Final Approach (Patreon)

Let’s say it was the end of 2023 before I reached the final thoughts I shared in my last chapter. I would sit on my thoughts torn between thinking I should call and believing it was too late.

“Not today” became “not this week” and eventually I decided too much time had passed. I knew Ailana had decided I had abandoned her. She had figured I was just one more person who had come into her life and eventually moved on.

The year 2024 was in full swing and I was doing well on the job. Socially, I was doing nothing.

None of the women I met got past the gate of my memories of how things had been with Ailana. I know we had been apart for years, but engraved in my thinking was a standard for what I wanted—a standard that included intangibles that I could not even articulate, yet they were real enough that I knew when they had not been met.

Looking back, I think that year was exactly what I needed to finally close the circle of my thoughts. I fully acknowledged the ideas of grace that Steve McDonald discussed. I fully accepted Dr. Matthew’s suggestion that what she did was not who she was.

I was left with my regrets. My decision to go to Venezuela seemed questionable. My failure to call when I returned was clearly a mistake. By summer 2024, I believed I’d forever lost Ailana and settled down for what I thought would be years before I found someone who would—I hoped—fill the void she left empty.

Most who are reading this know that everything eventually worked out. It started in early February 2025, when she reached out by email to ask to use the Buckley Homestead anecdote in “Growing Up Ailana.”

The rest of this chapter is exclusive to Patreon.

After agreeing to allow her to tell the story we had promised to keep secret, I felt utterly unsettled. A piece of my past—of the past we shared—was so meaningful she wanted to share it with a growing social media following.

Before that discussion I had no idea that she had social media. I indulged my curiosity and looked it up to see what she had said about Buckley.

Then I went back months to the fall of 2024 when she started sharing her life in The Journal (Ailana’s Diary back then). I read everything.

I could feel her pain when the summer of 2024 ended and other creators who had worked with her disappeared. I was happy that Sasha, Geoni, and Josh were traveling with her. I was shocked by what happened in St. Croix thinking that it could have gone differently and I’d never have the chance…

I didn’t finish the thought. I knew what I couldn’t put into words—not even in my thoughts.

I read everything from fall of 2024 until I caught up with her story on February 13, 2025. I was stunned that she was going home, back to Indiana.

I suppose this is when my story started to merge with hers. On February 14, 2025, she finished “Growing Up Ailana.”

I sat in the waiting room of a doctor’s office, where I was making a sales call, and read it. It was strong.

I had left for Venezuela the summer of 2019. For over five years, I had drifted through life separated from Ailana. In the years since, I’d gone through a process.

On that day, the seed of understanding that I had come to from the mentorship of Steve McDonald and Dr. Matthew pushed a tender shoot up through the slowly thawing soil of my life. I knew I should reach out.

But I couldn’t. It was Valentine’s Day, and I knew that I didn’t want what I hoped would happen to ever be deemed a kitschy response to the cliché of cupids and red hearts.

I’d waited years. I’d wait until Sunday.

From "It Should Feel Like Home (Diary)"

Goodnight friends. To those of you sharing Valentine’s night with someone dear, I hope your evening exceeds your fondest expectations!

I am at the Denny’s in Hebron, drinking some coffee and reliving some memories. You may recall this location was mentioned in “Growing Up Ailana.” Of all the things I have shared, that moment may have been the one most dear to me. So long ago… So many decisions since…

On the 15th, she wrote an epilogue to the collection.

In it, she said:

From "GROWING UP AILANA ~ Epilogue"

I was born on Jan 1, 1997, on the day my mother called the day after her last day of happiness. I grew up pressured to be what my mother thought others expected me to be. Ultimately she gave up and left.

My father and I struggled year after year, frequently lacking money for utilities and skimping on food…

…

So, I entered 2024 with self-doubts, fears of being rejected, being left out, but a heart that believed that good people can rally into difficult situations and do good things for others.

I embarked on the journey of a digital content creator. And made mistakes…

…

The year led me into a fast-paced on-the-go lifestyle. It gave me the chance to shine a light on a lot of issues. But that pace caused me to drift… to drift away from… things… people.

My “Growing Up Ailana” project was started to answer questions from readers about my past. It ended up leaving me to ask questions about my future. I need to make a few little changes.

I need to organize my adventures so that I can keep in contact with my family.

Church was a core component growing up. I need to stop watering down my beliefs.

I have let a C. S. Lewis quote guide my work: “What we want is not more little books about Christianity, but more little books by Christians on other subjects—with their Christianity latent.” I will continue to do so. But, I need to acknowledge more often what I’m doing on Sunday mornings.

I am prepared to be judged…

…

So, I approach a year as a digital content creator.

I still doubt that I’m good enough. I still assume I’m easily overlooked; liked one moment, forgotten the next. I still think reputations are the vessel for credibility.

I still think that everyone can do something for someone somewhere. That people are worth helping, worth giving a chance.

What else will change as I grow from what I learned? Compared to Jan and Feb, not much!

I almost called at that moment, but I waited. On Sunday after church, on February 16, 2025, I finally made the call I should have made much sooner.

Our lives reconnected that day, and she wrote about it. I’ll share some of what she wrote that I think finally put us on the path that has for over a year led to what will happen on May 23, 2026—on that day, Ailana will take me as her husband.

On the 16th, I reached out and she wrote…

From "Looking Forward (Diary)"

Called

I had just returned to the hotel from church and changed clothes when I got a text message. I expected it would be from Sasha or Geoni, possibly Dad. It wasn’t.

It was a selfie from Jason. Yes, THAT Jason.

And a short text: “Can I call you?”

I figured he had changed his mind about letting me reference him in the backstory and wanted me to redact him out.

I said yes, of course. He called right away.

“Hey… Um… Since you called about the log cabin story… I’ve…” He paused, then changed directions. “How was your week? Your Grammy broke her face?”

I went with the flow and told him about my Dad's hospital visit, then I said, “What about the log cabin?”

“Yeah… I… read the Epilogue…”

“I’ve had a lot to think about…” I wasn’t sure where he was going.

“I… read pretty much everything going back to… like August… St. Croix… wow, that was…”

“Yeah, I should have been more careful.”

“I bet you were scared…” We talked about that, but I was sure it wasn’t his reason for calling.

Finally, he sort of moved toward… something. “So, you… haven’t dated?”

“I’ve been out a few times. Mostly modeling related. Nothing… meaningful.”

“Same…” Jason’s voice sort of quivered, but he went on. “So… we sort of… you called it drifted.”

“Yeah. You had… issues with my choice to do… certain kinds of modeling….”

“I guess you did, too?”

“Looking back… I’m not sure where the line was, but I crossed it. It was never… explicit… anything…”

“I know… I… just didn’t know… how to handle things… how to think…” Jason spoke in staccato. “Then… COVID… and all your traveling…”

I thought I should try to push the conversation forward. “So… why did you call?”

“Ailana, I want to… see you face-to-face. Maybe… un-drift… if…”

“Un-drift?”

“You know, we never officially broke up… I was on a few dates, and all I could think of was that I was cheating on you. It’s only been 5 years… I mean… yeah… that’s a lot… but…”

“Un-drift?” I said again.

I felt myself smiling genuinely for the first time in days. “We never did break up, officially, did we?”

“I know that’s semantics.” Jason replied. “But, things… drifted… with no real closure. No real ending… And really… the handful of dates I’ve gone on since college… I always thought about how things were with us… I… well… I don’t know if you get it but…”

“No… You’re right about there never being any closure. We should…” I wanted to say that we should just admit it was over; I figured that would be where it would end up anyway.

I know I still carry some soreness about his reaction to my mistakes with the modeling. But, I do see his point of view now, looking back. And, that one incident of disapproval is really the only thing I can claim he ever did that was disagreeable to me.

“Jason, you looked at my posts?”

“Back to St. Croix…”

“And you saw the pictures?”

“I read your Epilogue. You’re sharing your life. How you live. What you do. It’s like you’re a reality TV show. So… yeah… there's some intimacy to the pictures, if you just look at them. But, they are… slices of your life. I get it…”

“So you approve?” I felt my heart stop; the question reeked of my mother’s values. “I mean… do you think the pictures are keeping people from getting my messages?”

I heard Jason sigh. “Look… less than 1% of your followers comment meaningfully. So, maybe 10% read the post. What the others think, I can’t say, but anyone reading the posts knows what it is. You sleep in the buff. You… go natural… You do beaches. You take showers… So, if you’re asking me if I approve of those pics… Ailana, they go with your story. And I don’t think they hinder your message. And…”

“And?”

“I was going to say the fact you asked me if I approve… must mean… something…”

My stomach flipped. “Wow… Jason…”

The silence after that was long. Very long. I have no idea how long, but I eventually broke it.

“Where are you?”

“Memphis. The company has a condo on South Bluffs. Me and two other sales guys share it when we’re in town.”

“What’s the weather like?”

“Funny you ask… It was 70 last night. This week we might get snow…”

Goodnight

Well… Today… was… not without surprises. Different night. Different Denny’s. Different mood.

So many different ideas and feelings springing from a single phone call. And, I spent the afternoon with Dad and Grammy, so, I’ve not had much time to think.

So… That phone call… from Jason. I am speechless.

I have no idea what I’m feeling. I’m thinking that a trip to Memphis is crazy! It would be just insane to haul myself down there. Right? After five years, just fly 500 miles and… I don’t even know what the point would be!

Then, on the 17th, we talked again. This is her account of what happened…

From "Getting Data (Diary)"

Called Back

Since Dad is at work, and there was NO WAY I was going to spend the day drenched by Grammy’s on-going negativity, I decided I’d come to Indiana Dunes.

I just got off the phone with Jason. The call went like this:

Caller ID gave away my identity. “Hey… Ailana… good morning.”

“You busy?”

“Sitting at the gate… flight to Dallas. I have several day-trips lined up. What’s up?”

“I… Well, I had a hard time falling asleep.” I told him about the idea to move Dad and Grammy, then went on. “And, I was thinking about our talk yesterday.”

“I’ve been thinking a lot, too. I… hope you’re open to… getting together and talking.”

“I am… It’s just… You had a head start thinking about this… un-drifting idea.”

“A few days… It couldn’t hurt, right?” His tone was optimistic.

“True…”

A moment of silence followed then Jason said, “Ailana, let me ask you about your content creation…”

I figured he was going to have some things to say about my pictures. “Sure…”

“Are you making any money?”

I laughed. “Not much. Not enough to cover the expenses of creating the images. I guess I’m covering the cost of Photoshop, though.”

“So, why do you do it? It takes hours of time everyday… Aside from the fun… Why are you doing it?”

I was surprised by the question—by the whole direction of the conversation. “I guess… I hope… I hope maybe people will see the world differently.”

“Okay… business school mode… What’s your mission statement? What are you trying to do?”

Wow. We talked for a long time. I told him about the volunteer work and he mentioned my little motivational moments. Finally, he took a shot at summing up.

“So, you want people to know more about needs in the world, more about how to live better… you want to be an example?”

“I… guess that… sounds right…”

“How about this… ‘The purpose of AGI is to inform, inspire, and motivate people to become better versions of themselves and to see and respond to the needs of the world around them.’”

Silence and awe, then Jason said, “I think I’d like to be part of that.”

Goodnight

Let’s see… night… hotel… t-shirt… I must have a lot of work to do! (Laptop already booted up and waiting.)

Okay… I can’t NOT mention the call to Jason.

I guess I am braced for… not being accepted, not being included, not… Well, never mind all that.

Jason’s thoughts about what I’m doing really opened my eyes. In a single conversation, he sort of drew a box around what I’ve been trying to do. And… together (hold that thought)… we sort of drafted a fledgling mission statement for AGI.

…

I’m left with, once more, my thoughts spinning. Where I expected to be judged, I was affirmed. We revisited all that happened five years ago when we (as I called it) drifted apart. Neither of us feel like any permanent damage was done.

I guess that leaves me open to the idea that, at least as a partner in AGI, Jason could…

I can’t believe I’m saying this… In fact, I’m not ready to say it.

But, when I think about how much better things became once Sasha took over project managing, I can’t help but entertain the idea… Plus, he’s a great photographer.

Yeah… I’ll get to work now.

The next day, my world transformed. What happened that day lifted a weight from my shoulders that I didn’t know I’d been carrying since 2019…

From "Mission Minded (Diary)"

Planning To Plan

Trying to get some work done from the hotel before I go over to spend the evening with Dad and Grammy. I… made the call to Jason about… I can’t believe it, but I’m going to Memphis.

Here’s how it went. I texted him a while ago and said, “Hey, call me when you have time.”

Thirty seconds later he called. “Hey! Surprised to get your message. What’s up?”

“Are you busy? It sounds noisy.”

“About to get on an elevator to the respiratory therapy unit. I’m with a company doctor. He gets to tell all about the meds and I get to tell about ordering, shipping, storage, and the pipeline…”

“So you’re busy?”

“They can wait. I’d rather talk to you.”

At that point, I think my stomach remembered what it was like to be 17! “Will you still get back to Memphis tomorrow night?”

“Yeah… 8:35 says the ticket… I’d call you tonight, but I know you’ll be with your dad. I have a dinner meeting anyway. Want me to call you in the morning?”

I smiled, though he couldn’t see it. “No… don’t call. I’ll just talk to you when you get off the plane. I’ll grab the gate number off the board in the airport. American Airlines… Dallas to Memphis?”

“Yeah… American… what do you mean?”

“I’ll see you at the gate when you get off the plane…”

“Wait! What? Really?”

“Yeah,” I replied. “I want to get into that idea you had about… being part of AGI and… mostly… about un-drifting… I think.”

“You think?”

“Something… There’s a lot to think about… so…”

“Okay…” Jason sounded pleased. “Okay… so… yeah… see you… in Memphis… Wednesday night… wow…”

I heard someone calling his name from nearby. “Okay… I… have to go.”

“Okay… bye.”

~~~

So, that happened. I just have to get to Memphis tomorrow before he does. Also, plot twist: Memphis is supposed to get snow overnight tonight, so no telling what is going to happen! I might need to take a snow shovel!

From that point, I feel like her diary entries carry the story onward. However, I do want to include final excerpts from the 19th and 20th which I think set the course that we’ve walked ever since…

From "To The Bluff City (Diary)"

Goodnight

Well, it’s not Denny’s, but IHOP’s “Big Country Breakfast” is close enough to a “Lumberjack Slam.” We feel like it’s a good alternative place to eat.

I used “we” in that last sentence. It felt different than other “we”s I’ve used when I was talking about Sasha and the others.

I met Jason at the gate. I spotted him first, and when he saw me, his face lit up. And that made my stomach go flippy. But, never mind that for now.

He came to me, stopping a step or so back. “Wow… you look beautiful!”

I felt myself blush as I looked down. “Thanks…”

Jason laughed. “So… I’ve been planning what to say when I saw you since take-off. That’s not what I planned!”

I looked up and laughed. “Plans have a way of going like that…”

“Yeah…”

“What had you planned to say?” I asked.

“I… wasn’t committed, but, ‘Hey… long time, no see’ was not on the list! I wanted to… be… real… Something to the effect of ‘I’m really glad you decided to meet.’ And I was going to let you know I would have come to Indiana.”

“Well, I guess I have an easier time being flexible. So…” I shrugged.

I felt like I needed some air… and space. So, I asked him to tell me about his trip and the meeting at the hospital. That got us to my rental car. I know it was sort of a contract breach, but I let him drive.

By the time he backed out of the space, it felt like old times. Him taking me home from softball practice. I almost reached for his hand to hold it!

The conversation became liquid and by the time we got to IHOP, we were filling in details over the last 5 years, each in turn sharing events and experiences.

So, that’s kind of where we are right now. I told him I’d post this, and he said he was okay with that.

“Hey… if things go like I hope… I’ll… have some part in your reality show, right?” He smiled. “Ailana Geven… flagship for AGI Stories… Slices of life, moments of inspiration, leading by example… Like I said… I’d like to be part of that…

Yeah… that happened. Again.

…

From "So Begins What? (Diary)"

Goodnight

I’m back in the hotel. I dropped Jason off at the airport for his red-eye to Atlanta.

We had a nice dinner…

Well, Jason said he had written something and would send it from the plane. He said I could share it, so…

Ailana,

Since you called about the log cabin story, my thoughts have been distracted. A lot.

In the five years that we… drifted… I can honestly say I thought of you regularly. I wish I had known about your social media right from the start; I imagine I would have reached out to you along the way.

Having read everything you have posted and us sharing 10 years together leave me feeling like I know you pretty well. At some point, you’ll ask yourself why I am trying to reconnect with you.

You’ll doubt yourself. You’ll think that you are less than you are, and that will make you imagine things about my motives.

“Why would he want to be part of MY life?” you’ll ask.

I could pretend that it is because I want to be part of something special. Anyone can put on a tie and talk about the ordering process and pipelines. Sure, our products help people.

But, what you are doing is special. You are opening eyes to the needs of the world.

I could pretend that alone fostered my interest in AGI Stories. That it was my chance to get out of the airport and make a difference.

While that is true, it is incomplete. And secondary.

I know it was 5 years ago, but we were 23 and had been together 10 years. That is not insignificant. My heart longs to pick things back up and see if we can resume building on that abandoned foundation… To deny that would be a lie.

And, if I can also add value to AGI, then all the better.

Please give this some thought.

Jason

Okay, I’ll be in bed thinking about this for a while.

So, from that point forward, Ailana and I began walking together on a path—at first, the destination wasn't clear. I came to know where I hoped it would lead a little before she did. It turns out, it leads to our wedding.

I’m not going to write an epilogue. For that, I’m going to invite you to go back to all that’s happened since Ailana arrived in Memphis at the end of February, 2025.

I do not appear in the Journal often. But I’ve been there, at her side, almost every day. It was a long path that eventually led to a place where Ailana was finally ready to say yes.

The close of my series isn’t really an ending. It was the introduction to the fifteen months that followed leading to the wedding soon to come.

And the wedding isn’t an ending either. Far from it!

On May 23, 2026, begins, not a new Journal entry, not a new chapter, but an entirely new season. It is my hope that this collection of my thoughts helps you see who I am and understand how I came to be this way.

Thank you for taking the time to get to know me better. I’m looking forward to, in the months and years to come, being the guy behind the camera and beside the words of Ailana’s Journal.

Be your best you!

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All characters in this story are fictional characters, their images generated with AI for AGI Stories. They do not represent any real person, nor is their appearance based on any real human.

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