My Engagement Story
First of all, who proposes on a Monday?
Brian does!
And honestly, as an extremely observant, smart cookie, I’m still trying to understand how he pulled off something so elaborate, intentional, and wildly surprising without me having even the slightest clue.
June 8th, 2026. Exactly 18 months to the day of our first date.
But this story really starts months earlier.
Brian had been planting seeds for a while and I, completely unsuspecting, was watering every single one. Let me back it up.
I can trace it back to February when Brian, unknowingly (since he didn’t have any sort of timeline yet), planted his first seed.
The seed that would become the biggest decoy in his masterful surprise.
Brian told me that his parents wanted to meet my parents before we got engaged. Since they live in different states, the earliest weekend we could coordinate everyone’s schedules was June 19th (Father’s Day weekend). Naturally, I did what any rational woman would do. I created a timeline in my head. I figured if it didn’t happen by May, then it was either happening June 19th weekend (which honestly felt way too obvious) or sometime after June 26th once our families had officially met and we were back in LA.
Fast forward to early May when Brian, now knowingly, planted the second seed. Brian and I were having one of our standard money conversations. Discussing the reality of being two entrepreneurs where our incomes look different month-to-month. I remember Brian reassuring me that June will be a great month because he had just spoken to his colleague Jason, who was likely booking him for a big keynote.
For more context, Brian often works with Jason, a founder of a leadership development and speaking company. Jason frequently brings Brian in to support corporate offerings by co-leading offsites, workshops, and keynotes.
A few days later, a calendar invite titled “BMO Offsite + Keynote with Jason” landed in my inbox, and I accepted it without a second thought.
The brilliance of Brian’s plan was that every detail was so grounded in our actual life. Nothing felt suspicious. The only thoughts I had were:
How excited I was for Brian.
How eager I was to finally meet Jason, given how closely they work together and how he’s become a household name, yet I’ve never personally met him.
To fully appreciate how flawless Brian’s performance was, here’s how specific he got with the details.
He told me:
The offsite was for BMO, a company I already knew Jason worked very closely with and would be doing a lot of work for in the coming months.
It was for a 12-person executive leadership team plus spouses because the retreat only happens once a year and they liked investing in both the executives and their families.
There was separate daytime programming for spouses while the executives attended strategy and development sessions.
The offsite began on Sunday, June 7th, with Jason hosting a kick off event, and ended on Tuesday, June 9th.
Monday night (June 8th) there would be a client dinner at 6pm that Jason wanted us to attend.
Tuesday morning Brian would lead his signature MAGIC keynote at 9am.
And for extra credibility, this exact schedule (dinner the night prior to the keynote) had been the format of previous corporate gigs Brian + Jason led together. No wonder I was completely fooled!
As we got closer to the event, Brian kept feeding detail after detail to keep the story airtight, and he had quick, very normal responses for my many questions:
I asked if we were staying in Malibu overnight, so we didn’t have to drive back and forth from Santa Monica for the two events. He said he wasn't sure yet, but he'd check with Jason to see if he could get us a room. Keeping me on my toes, two days before I asked again “Wait, were we able to get a room at the hotel? To which Brian replied: "Oh yeah, Jason took care of it, we’re good."
I asked what the programming consisted of. He casually answered with: “Monday is strategy-focused with a client dinner we are expected to attend, and Tuesday is all about team-building.”
I asked about attire, Brian replied: “Want me to text Jason and ask? I can see what his wife is wearing too.” I declined and said I would figure it out because I didn’t want to bother Jason.
I asked if we’d be back in Santa Monica by 3pm Tuesday because I wanted to book appointments. Brian said: “Yeah, we’ll be done by then.” So, of course, I booked two appointments for Tuesday afternoon.
MONDAY MORNING
I wake up to Brian packing the supplies he usually uses for his keynotes: Hit of Happiness merch, a portable speaker, pens, notepads, etc.. I asked Brian if he wanted to review his keynote material, as we usually do, bouncing ideas off one another to refine our talks. He said: “yes, but after my run.”
All very normal behavior.
Right before I begin my workday, Brian says: “I just got off the phone with Jason. The kick off last night went really well. He's starting strategy sessions soon, and I recommended we use Human To Human (my conversation starter card game) for dinner tonight. He loved the idea. Do you mind going through the deck and picking the best question for us to use?” Of course, I say.
I sit down at our kitchen table sifting through 100 questions to hand select my favorites. “All done”, I say, “and actually why don’t you gift each exec a game after your keynote, I think it would be a nice touch (plus it’s good exposure).”
There I was, oblivious in helping to prepare my own engagement. I’m not sure how Brian stayed so cool, calm and collected. If it were me, I’m not sure I’d be able to hold back a huge grin and control my laughter.
YOUR INTUITION KNOWS THE WAY
Side bar, my intuition absolutely knew a lot more than my brain did. The Friday before (June 5), I was debating with Brian whether to get a manicure Sunday (pre-engagement) or Wednesday (post-enagement). With things like this, Brian lets me verbally process myself into my own conclusions. Despite knowing exactly what was coming, he stayed completely in character. He listened to me blab and never offered his opinion, because if he did, it would have been a dead giveaway.
So thank you intuition. Because for reasons I still cannot explain, I booked my nail appointment on Sunday afternoon, just 24hrs shy of the most important moment for me to have a fresh mani.
My intuition also picked out my outfit. I left for Malibu wearing jeans and a tank top assuming we’d arrive and head straight to dinner. Seconds before we left home, I casually thought: “Well… we’re driving so I basically have unlimited packing space. Let me throw in a dress.”
I never planned on changing that night, but as we were leaving our hotel room for the ‘executive dinner party’, I decided to change into the ‘backup dress’. Again, no explanation for why I was prompted to do that. All I know is that my gut decisions served me very well.
THE ARRIVAL
We checked into Calamigos Ranch around 5pm and were welcomed by Kurt, the concierge behind the front desk. Brian tells him: "We’re here with BMO for the executive offsite."
With a big smile and without hesitation Kurt responds: "Amazing, we’ve been expecting you. Everything has been going great so far. And good news, they actually upgraded your room. I’ll take you there now and your dinner event starts at 6pm, so I’ll come back to pick you up at 6pm."
At this point literally everyone knew except me. Brian had recruited Kurt into his operation when he scheduled a site visit two weeks ago.
We dropped our stuff off in our incredible room (Brian really went all out), explored the property for a few minutes, then Brian told me he had to head back to the room to iron his linen shirt. Which totally tracks because his linen shirts are always creating extra work and he hates the fact that ‘they always wrinkle’ 😂.
We’re walking out the door when I stop him and say: “Brian wait, don’t forget Human To Human.” His arm flings up into the air, waving the game around: “Yup, I got it!”
At 6pm sharp, Kurt returns, and instead of walking us to dinner, he drives us. Across what was essentially a gravel parking lot. The ride was 15 seconds tops. Brian and I are laughing in the back seat, thinking we could have just walked.
Staying fully committed to the bit, Brian says: "What a great touch and excellent customer service, I guess this is a good way to create a memory.” I agreed, thinking it was a unique gesture of excellent hospitality. Unbeknownst to me, it was really a ‘going the extra mile’ moment to make every detail about the engagement extra special.
We hopped out of the car and followed Kurt towards the barn, where said ‘dinner party’ was taking place. Kurt, maintaining character, said: “Let me sneak you two in through the back door. The event has already started.”
We reach the back entrance, Kurt tries the door, and it’s locked. Without missing a beat Kurt quickly says: "Oh, don’t worry this happens all the time, let's go around this way."
We hook a left and begin walking around a massive tree. A tree positioned so perfectly it blocked the entire proposal setup when we initially walked toward the barn.
As we rounded the corner, there was no Jason, no executives wearing suits, no dinner party. Instead, I was met with candles, flowers, string lights, a waterfall…and my jaw somewhere near the ground.
I was completely stunned and speechless. First came disbelief, then an all-consuming, intoxicating joy. I felt this overwhelming rush of love that even now, as I sit here writing this, I can feel myself transported right back into that exact moment. Still giddy, still in awe, still pinching myself to believe it was real.
As Brian walked me closer, his words were brief, but exactly right.
“So there is no keynote or dinner.”
Then he said: “Chloe…this is life beyond the dream."
(A meaningful and very fitting quote from his favorite band, Phish)
He got down on one knee and opened the Human To Human card game. But instead of cards, I saw another box. He had hollowed out the entire game to perfectly hide and hold the ring box.
“I love you, will you marry me?”
I said yes before he could even finish asking, and not even 30 minutes later, my cheeks were aching from carrying the biggest, longest smile I'd ever worn.
Brian had thought through every single angle and made sure that I had absolutely no idea. Truly not one instinct nor one suspicion, making it even more magical and epic than I could have ever imagined.
I have never felt more loved or cared for. It wasn’t just that he planned a beautiful proposal. It was that he paid attention. To what I would love, to what would surprise me, to every detail he knew I would notice, and to creating a moment so deliberate, deeply meaningful, and unmistakably ours.
I think that may be one of the greatest feelings in the world. To be loved not just deeply, but specifically and intentionally.
