From the Tree of Life to the Treasure: Family, a New Fiancé, and the Full-Blown Planning Chaos for a Party of 12 (WDW & DCL Sept 2025) Updated 11/14!!
- Thread starter KJeff90
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KJeff90
Mouseketeer
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- Apr 1, 2011
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Chapter 6 - "#super-secret-side-quest"
Hey there, friends! Thanks for sticking with me. I know I left things on a cliffhanger last time, and this next post is one I’ve been both dreading and excited to share. So hang on to them hats and glasses, because we are diving into the most chaotic thing I had to plan for this whole trip… the proposal.
(In Jordan Fisher Voice a la Happily Ever After)
"Ready to Begin..."
Picture it. It’s late March-ish, and all planning momentum has stopped dead in its tracks. Flights are booked (probably too early, but it’s fine, that plotline changes later). We picked All-Star Music for the pre-cruise stay, we penciled in a post-cruise hotel, and now we’re stuck waiting for port adventure booking day. The Disc0rd chat? Silent. Almost too quiet.
So my restless little brain does what it always does… it finds something else to obsessively plan. And that “something else” was tiny. No big deal. Nothing stressful at all. Just… planning to propose to my boyfriend of 15 years.
It had been on my mind for a while; some may even say far too long. But regardless of how many years we’ve been together, this just felt like the right moment to finally ask the question. Sure, part of it was because I suddenly had nothing left to plan… but at the heart of it, there was something deeper. There was genuine love fueling this whole endeavor.
The ring may have been bought back in April for this September trip and proposal, but I needed every minute to plan for that special moment.
Who Do I Tell?
Aside from my boyfriend, I was traveling with ten other people (one still in the womb). So naturally, I had to loop everyone in on the fact that Operation Proposal was starting. Well… everyone except my brother. Bless his soul, but that man could not keep a secret if his life depended on it. Respectfully. Lovingly. Factually.
Which is how we ended up with a hidden Disc0rd channel for the cousins: #super-secret-side-quest. Literally all discourse went down here. Announcing that I was doing it, sharing plans, spiraling, revising, and of course… seeking validation from the cousins.
This was also when I realized it was ChatGPT’s moment to shine. It let me ask the questions I didn’t feel ready to ask anyone else. It helped me run through logistics when all the real people were asleep. And, most importantly, it kept my thoughts and plans organized when everything felt too big to hold alone.
The Planning Actually Begins
The [Disney] World was literally my oyster of opportunity to do this. With our redeye flight already booked, I technically had the better part of our one and only pre-embarkation day to roam around WDW and get the deed done. At the beginning, we didn’t have any park plans at all. The only thing locked in was the two Family Suites at All-Star Music. What’s funny is… all of that changed.
I knew I wanted something beyond the classic, slightly overdone proposal in front of Cinderella Castle at Magic Kingdom. No offense to anyone who’s done it, but the two of us don’t have any emotional connection to that castle.
If anything, I would’ve proposed in front of Sleeping Beauty Castle at Disneyland, a place we both actually worked and have history with. (Oh, did I forget to mention there was a point where we were both Cast Members at the Disneyland Resort? Yeah. That was a thing.)
I genuinely considered all four parks, the ship, the airport, and even the planes. If we were going to breathe the same air as it during the trip, it made the list of potential proposal locations.
One Thing Lead to Another, and Bing Bang Boom
Initially, I knew my boyfriend and I both had a very real, very deep love for Animal Kingdom. It is our kind of park: immersive, atmospheric, emotional, and honestly underrated. But even with that in mind, I kept straying away from the idea of buying a park ticket for just one day.
Why? Because all the usual reasons lined up one after another. The park closes early. We would be coming off a redeye, which meant a guaranteed late start and absolutely no rope drop. We already had a free waterpark day included with our stay at All-Star Music. And the biggest reason of all was simple: it costs more money. Every logical bone in my body (there aren't that many) kept saying, “Jeffrey, stop. Be practical. Don’t do this.”
So backup plan B came into play, still thriving on nostalgia and a desire to reach that happily ever after. I thought of the next best thing. We had always wanted to stay at Animal Kingdom Lodge, but never had the opportunity to. At this point I was not willing to spend more to visit Animal Kingdom Park, and I was definitely not going to splurge on a stay at the Lodge.
I remembered that iconic bridge in their lobby, and I thought it was the logical choice. I could just find our way to the Lodge and pop the question either before or after our waterpark day. Things were set.
But as you will see very soon, logic did not stand a chance. Who is she?
"It Wouldn't Be That Much More…"
Well, it seemed almost too easy to settle on that idea. It felt majestic and opportunistic if you will. But something kept irking me. It felt like I was missing something, like the moment I had imagined was not quite there yet. The sudden quiet with nothing left to plan was hitting hard, and my restless self kept wandering back to the internet looking for inspiration.
I kept wondering how I would even get to Animal Kingdom Lodge when a waterpark day and a stay at All-Star Music were already in play.
Curiosity got the best of me, and that is when I discovered Dave’s DVC Rentals. That is when I also realized the magic of booking through a third party and doing a points stay. Suddenly a three-bedroom Grand Villa at most DVC resorts was technically less than booking five Moderate Standard rooms at rack rate. Sure, we already had two Family Suites at All-Star Music with technically enough sleeping spaces to fit all twelve of us, but Disney trip planning math surpasses real math.
For only a “tad” more, and by “tad” I mean “double,” we could get a three-bedroom Grand Villa at a DVC property. So I put in the request for a one-night stay on the Dave’s DVC site and figured it would take a while to get approved. I had already come up with multiple backups, which I submitted in order of preference: Disney’s Animal Kingdom Lodge with Kidani Village as the top choice, then Boulder Ridge Villas at Wilderness Lodge, then Disney’s BoardWalk Villas.
Within about three days, it got approved. Before I knew it, I was paying in full for our three-bedroom Grand Villa at Kidani Village. And yes, it was significantly more affordable than the cash rate. Also don’t worry, I didn’t surprise my cousins with this new expense. I paid for this "upgrade" on my own. I told them about it well before we started the trip, so it wasn't an "in-the-moment" surprise. This is how I teased it to the cousins (...don’t get it? Neither did they).:
And all of this was simply to make the logistics a little smoother so I could get to that Jambo House bridge for the proposal.
"Oh Look, A Park Day Wouldn’t Be That Much More Either…"
Yeah, this restless mind also discovered that a day in the park for my boyfriend, my brother, and me would not be a deal breaker. So I did what any reasonable, responsible planner would do. I booked Animal Kingdom tickets for that Disney World day before embarkation. Sure, it was a “late start,” but I figured we could still get into the park by around nine in the morning, which felt like a perfectly doable day.
And of course I could not stop there. I kept going and booked this sucker:
I booked it for 10:30am in the morning, giving us enough time to grab a light breakfast and then head into the Capture Your Moment session. The plan was simple. Propose during the session and then celebrate with a more significant lunch right after. The cousins wanted to be part of the celebration too and suggested Jiko for dinner back at the resort after our day in the park and their waterpark day. We booked it for 7:20pm and 7:30pm (we had to split our party of 12 into two ressies). It seemed doable and it made sense.
This was also the moment where I took to the DisBoards community and asked for help, insight, and feedback. Here’s the post that grabbed interest from the community:
https://www.disboards.com/threads/ambitious-proposal-day-at-animal-kingdom.3971010/
About That “Significant Lunch”...
You would think planning a single meal after the proposal would be the easy part. You would be wrong. This is Disney. Nothing is ever that simple. What started as a nice, calm lunch idea spiraled into its own tiny side quest. For me, this became one of the most chaotic planning highlights. For others, it was the beginning of their villain origin story.
I had to reach out to ChatGPT for the receipts of our talks, but here are the stats of this not-crisis… crisis, lol:
The Plan So-Far (For Now…)
At this point, everything looked like it was finally falling into place. We had a park day, a Capture Your Moment session, a lunch plan that had survived too many identity crises, and a celebratory dinner that sounded elegant and calm. It was all coming together… or so I thought.
At this point, this is what we have planned for “Proposal Day”:
Hey there, friends! Thanks for sticking with me. I know I left things on a cliffhanger last time, and this next post is one I’ve been both dreading and excited to share. So hang on to them hats and glasses, because we are diving into the most chaotic thing I had to plan for this whole trip… the proposal.
(In Jordan Fisher Voice a la Happily Ever After)
"Ready to Begin..."
Picture it. It’s late March-ish, and all planning momentum has stopped dead in its tracks. Flights are booked (probably too early, but it’s fine, that plotline changes later). We picked All-Star Music for the pre-cruise stay, we penciled in a post-cruise hotel, and now we’re stuck waiting for port adventure booking day. The Disc0rd chat? Silent. Almost too quiet.
So my restless little brain does what it always does… it finds something else to obsessively plan. And that “something else” was tiny. No big deal. Nothing stressful at all. Just… planning to propose to my boyfriend of 15 years.
It had been on my mind for a while; some may even say far too long. But regardless of how many years we’ve been together, this just felt like the right moment to finally ask the question. Sure, part of it was because I suddenly had nothing left to plan… but at the heart of it, there was something deeper. There was genuine love fueling this whole endeavor.
The ring may have been bought back in April for this September trip and proposal, but I needed every minute to plan for that special moment.
Who Do I Tell?
Aside from my boyfriend, I was traveling with ten other people (one still in the womb). So naturally, I had to loop everyone in on the fact that Operation Proposal was starting. Well… everyone except my brother. Bless his soul, but that man could not keep a secret if his life depended on it. Respectfully. Lovingly. Factually.
Which is how we ended up with a hidden Disc0rd channel for the cousins: #super-secret-side-quest. Literally all discourse went down here. Announcing that I was doing it, sharing plans, spiraling, revising, and of course… seeking validation from the cousins.
This was also when I realized it was ChatGPT’s moment to shine. It let me ask the questions I didn’t feel ready to ask anyone else. It helped me run through logistics when all the real people were asleep. And, most importantly, it kept my thoughts and plans organized when everything felt too big to hold alone.
The Planning Actually Begins
The [Disney] World was literally my oyster of opportunity to do this. With our redeye flight already booked, I technically had the better part of our one and only pre-embarkation day to roam around WDW and get the deed done. At the beginning, we didn’t have any park plans at all. The only thing locked in was the two Family Suites at All-Star Music. What’s funny is… all of that changed.
I knew I wanted something beyond the classic, slightly overdone proposal in front of Cinderella Castle at Magic Kingdom. No offense to anyone who’s done it, but the two of us don’t have any emotional connection to that castle.
If anything, I would’ve proposed in front of Sleeping Beauty Castle at Disneyland, a place we both actually worked and have history with. (Oh, did I forget to mention there was a point where we were both Cast Members at the Disneyland Resort? Yeah. That was a thing.)
I genuinely considered all four parks, the ship, the airport, and even the planes. If we were going to breathe the same air as it during the trip, it made the list of potential proposal locations.
One Thing Lead to Another, and Bing Bang Boom
Initially, I knew my boyfriend and I both had a very real, very deep love for Animal Kingdom. It is our kind of park: immersive, atmospheric, emotional, and honestly underrated. But even with that in mind, I kept straying away from the idea of buying a park ticket for just one day.
Why? Because all the usual reasons lined up one after another. The park closes early. We would be coming off a redeye, which meant a guaranteed late start and absolutely no rope drop. We already had a free waterpark day included with our stay at All-Star Music. And the biggest reason of all was simple: it costs more money. Every logical bone in my body (there aren't that many) kept saying, “Jeffrey, stop. Be practical. Don’t do this.”
So backup plan B came into play, still thriving on nostalgia and a desire to reach that happily ever after. I thought of the next best thing. We had always wanted to stay at Animal Kingdom Lodge, but never had the opportunity to. At this point I was not willing to spend more to visit Animal Kingdom Park, and I was definitely not going to splurge on a stay at the Lodge.
I remembered that iconic bridge in their lobby, and I thought it was the logical choice. I could just find our way to the Lodge and pop the question either before or after our waterpark day. Things were set.
But as you will see very soon, logic did not stand a chance. Who is she?
"It Wouldn't Be That Much More…"
Well, it seemed almost too easy to settle on that idea. It felt majestic and opportunistic if you will. But something kept irking me. It felt like I was missing something, like the moment I had imagined was not quite there yet. The sudden quiet with nothing left to plan was hitting hard, and my restless self kept wandering back to the internet looking for inspiration.
I kept wondering how I would even get to Animal Kingdom Lodge when a waterpark day and a stay at All-Star Music were already in play.
Curiosity got the best of me, and that is when I discovered Dave’s DVC Rentals. That is when I also realized the magic of booking through a third party and doing a points stay. Suddenly a three-bedroom Grand Villa at most DVC resorts was technically less than booking five Moderate Standard rooms at rack rate. Sure, we already had two Family Suites at All-Star Music with technically enough sleeping spaces to fit all twelve of us, but Disney trip planning math surpasses real math.
For only a “tad” more, and by “tad” I mean “double,” we could get a three-bedroom Grand Villa at a DVC property. So I put in the request for a one-night stay on the Dave’s DVC site and figured it would take a while to get approved. I had already come up with multiple backups, which I submitted in order of preference: Disney’s Animal Kingdom Lodge with Kidani Village as the top choice, then Boulder Ridge Villas at Wilderness Lodge, then Disney’s BoardWalk Villas.
Within about three days, it got approved. Before I knew it, I was paying in full for our three-bedroom Grand Villa at Kidani Village. And yes, it was significantly more affordable than the cash rate. Also don’t worry, I didn’t surprise my cousins with this new expense. I paid for this "upgrade" on my own. I told them about it well before we started the trip, so it wasn't an "in-the-moment" surprise. This is how I teased it to the cousins (...don’t get it? Neither did they).:
And all of this was simply to make the logistics a little smoother so I could get to that Jambo House bridge for the proposal.
"Oh Look, A Park Day Wouldn’t Be That Much More Either…"
Yeah, this restless mind also discovered that a day in the park for my boyfriend, my brother, and me would not be a deal breaker. So I did what any reasonable, responsible planner would do. I booked Animal Kingdom tickets for that Disney World day before embarkation. Sure, it was a “late start,” but I figured we could still get into the park by around nine in the morning, which felt like a perfectly doable day.
And of course I could not stop there. I kept going and booked this sucker:
I booked it for 10:30am in the morning, giving us enough time to grab a light breakfast and then head into the Capture Your Moment session. The plan was simple. Propose during the session and then celebrate with a more significant lunch right after. The cousins wanted to be part of the celebration too and suggested Jiko for dinner back at the resort after our day in the park and their waterpark day. We booked it for 7:20pm and 7:30pm (we had to split our party of 12 into two ressies). It seemed doable and it made sense.
This was also the moment where I took to the DisBoards community and asked for help, insight, and feedback. Here’s the post that grabbed interest from the community:
https://www.disboards.com/threads/ambitious-proposal-day-at-animal-kingdom.3971010/
About That “Significant Lunch”...
You would think planning a single meal after the proposal would be the easy part. You would be wrong. This is Disney. Nothing is ever that simple. What started as a nice, calm lunch idea spiraled into its own tiny side quest. For me, this became one of the most chaotic planning highlights. For others, it was the beginning of their villain origin story.
I had to reach out to ChatGPT for the receipts of our talks, but here are the stats of this not-crisis… crisis, lol:
ChatGPT said:
The Plan So-Far (For Now…)
At this point, everything looked like it was finally falling into place. We had a park day, a Capture Your Moment session, a lunch plan that had survived too many identity crises, and a celebratory dinner that sounded elegant and calm. It was all coming together… or so I thought.
At this point, this is what we have planned for “Proposal Day”:
- Arrive at MCO around 6:00am.
- Meet up with our Private Transfer to Kidani Village at around 6:30-6:45am(ish).
- Get to Kidani around 7:30-8:00am(ish).
- Room won’t be ready, so drop off bags with Bell Desk and stop by the Front Desk.
- Maybe go to Sanaa for a quick breakfast, or at the Mara at Jamb House, for breakfast.
- Go our separate ways at 9:30am(ish). Cousins to Waterpark, My bro, boyfriend, and I to Animal Kingdom.
- Capture Your Moment at 10:30am. (Proposal Time!)
- Lunch at either Tiffins or Tusker House at 11:30? (Still figuring it out at this point).
- Spend the rest of the day in Animal Kingdom until 5:30pm(ish). The park closes at 6:00pm.
- Check into Villa at Kidani Village and get ready/dressed for 6:30(ish) ressies at Jiko to celebrate with the cousins.
- After dinner, go to bed and rest up for embarkation day.
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