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The Most Romantic Proposal

Updated: Dec 16, 2018

I've been the kind of girl who has wanted to get married since...well... since the day I put a white dress on my Barbie and made her enthusiastically say yes to Ken before darting off in their pink jeep on the way to the Barbie play house.


For me, always ambitious, I never felt "complete" unless I was with somebody else. I've always felt that a part of me was missing and there was a part of me that would be unfulfilled if I didn't "settle down."


Far from virtuous, I dated quite possibly every combination of man you could think of.


Let's see...

  • There was the redneck Romeo from my Georgia days; who taught me good ol' Southern values

  • An inner city immigrant who pushed through unimaginable poverty to make it to the United States after fleeing his country with his brothers and sisters; who taught me perseverance

  • The wealthy to do executive whose car was worth more than an entire years salary to me, who taught me all about sales processes and corporate leadership, and organizational structure

  • The chronic underachiever who was frequently talking about how he was going to do big things, but his love for the bottle never would get him out of his rut; who taught me about the dangers of short-term gratification

  • And of course, the misunderstood tattooed rebel without a cause; who taught me that once in a while, let go of your cares and free your soul to the world...


Each one, helping to shape me and define me in ways that made me better off despite some horrid breakups.


And then, in May or 2015, I met my Ken doll. I knew instantly, the moment I saw him rounding the corner of Tower 23 in Pacific Beach, California. We technically met online, therefore making this, our first date.


He approached me with his arms stretched out wide around his 5'10", athletic frame. A toothy wide-grinned smile took over his face and I stood up from the concrete block I was on, to meet him with an enthusiastic smile.


He was hot.


Errr...I mean...had a great personality.


What followed next was a series of drinks and appetizers for just a mere two hours before we parted ways, hoping there was a second date.


What most people don't know, was that weekend I had plans to move to Denver, Colorado to be closer to better healthcare system for my frequent Cystic Fibrosis flare-ups.


But as I looked at apartments, something in my heart told me to go back to California because there was something about this man, that was different.


Over the next 3 1/2 years, we would share in some unimaginable feats.

  • His business would really struggle, to the point he questioned his own abilities.

  • My health would begin to fail when I was denied a life-altering new market drug due to insurance and pharmaceutical battles.

  • I would get on national news with NBC's Lester Holt, pleading my case for the drug to which I would receive later that day.

  • He would be mixed in some terrifying legal battles by people he loved, over what seemed to me to be simple misunderstandings.

  • I would start a company to get off of disability services only to absolutely hate my day to day responsibilities

  • He would star in his own comeback story as I helped hire new staff for his business

  • I would spend days in seminars and diving into books from my hospital bed, only to have a burning desire to write my own nonfiction piece about emotional intelligence and mindset mastery

  • My book would hit #1 on several charts, catapulting me into speaking opportunities

  • He would settle all the confusing legal chatter and to celebrate, we would travel to Italy and over a Christmas break with his family, the Bahamas.

  • I would start getting booked every month for another speaking opportunity, making me realize I needed to shut down the business I had began to resent and pursue a completely different life path

  • We would start chatting about sales; to which I started helping his company, only to shatter old records and in the 6 months of my sales training, take the team to the top 2 best performing months in the entire history of the company

And then, after a particularly exhausting weekend, he asked me if we could go on a romantic date mid-week.


Something that after 3 1/2 years, we've never done.

My boyfriend is not necessarily a romantic. Nor is he one to take time off in the middle of a week for a date.


A few months ago, we travelled to Yosemite where underneath a starry sky, he attempted to propose with a promise ring to the tune of, "I don't want a dog and pony show. I'm like a squirrel, I know I need acorns but I'm afraid of acorns." I told him, marriage is and always will be a non-negotiable for me. However, I loved him and was not going to leave if he needed more time until he was as confident as I was on day one.


We laughed for hours that night at how awkward he was, as he explained that there would never be another woman for him and that he did want to marry me, just shy because he didn't know how and he admits, "You know, words just not good at like you." (He's actually a brilliant communicator).


He then asked me to plan my proposal so he didn't mess it up. I turned him down.


It was no surprise then when he asks for a romantic mid-day date that this was it.

The night before I got my nails done.

The day off I cancelled my appointments and had one of my best friends come over and do my makeup. We picked out my outfit and styled my hair the way Barbie would have looked, if she was 5'5" and 140 pounds.


And he picked me up from our beautiful apartment, where we said goodbye to our puppy and I took a deep breath, hoping I wasn't wrong, and I would come back home engaged.


Why hoping?


Because, this man in his enormous soul, can also be excruciatingly confusing.


We were in Venice, about to take a Gondola ride, when I thought for sure he would propose. He sits next to me at a cafe, overlooking the square, I was anticipatory as I thought the ring would be coming from his pocket, only to find out he wanted to ask if we could take a water taxi instead of the famous Gondola rides.


We were dancing at a bar one night, laughing hysterically as he put his arms around me and said he wanted to spend his life with me. I thought for sure, he was going to propose. He didn't.


He told me he booked a hot air balloon ride for one weekend in Temecula, a private ride over wine country, to which I definitely thought he would propose. Only to get a call a few hours later from him, asking if we could go to a baseball game instead.


My girlfriends and I nicknamed these moments, False Alarms...


There were way too many to count.


But as he drove me to a secret location on a random Thursday afternoon, I knew this wasn't the false alarm.


For the last 3 1/2 years, I spent considerable waking hours taking personal development courses, working on myself. I knew he didn't believe in marriage, he never has. He made that clear on our first date. But a lifetime with him, married or not, was enough for me and I got busy doing all the work I needed to do on myself, should he ever propose I was not going to build a marriage on baggage.


And I see the sign for the executive airport as he pulls in.


A plane? Are we taking a plane?


And then the sign for private helicopter tours.

Cue, "Mr. Grey will see you now."


We walk in the lobby to see a chilled bottle of champagne with a letter board that reads, "Happy Birthday Weekend". Eyeroll. Where's the "Will you Marry Me?" letter board.

Flowers in the shape of a heart wrap around a Godiva chocolate box.


This better not be a false alarm.


We take a golf cart to a private helicopter, where the driver insists on taking a few photos.

I think to myself, he's going to get down on one knee, right here.


I remember after the squirrel-acorn-yosemite-incident how I told him a dream proposal would be him getting down on one knee, so I figured now was as good as time as any for that gesture.


He didn't.


So I think, false alarm as my face twists in contempt as we board our helicopter, sans ring.


We fly up past the hospital I stay at, where we've had many dates.

The San Diego coastline where we've pub crawled and walked our puppy.

The different places we have lived.

Balboa park where he said he loved me for the first time.

Tower 23 where we had our first date.


The pilot is narrating the locations below us, I'm looking out the left side and he's peering over my shoulder. When he goes, "that's our first date, where I was hoping I could give you this." I look over at him.

Don't see a ring so just awkwardly ask what he's asking.


"Will you marry me?"


I look down. Confused.


Is this a real proposal, a false alarm, or a Yosemite moment?


It's a pretty big diamond, the guy I know doesn't believe in marriage or diamonds or big ones.

Or romantic mid-Thursday helicopter rides.


Or are these stories I tell myself to protect my heart, should anything actually happen to destroy our non-matriomony?!


"Ma'am?" The pilot ruins my thoughts.


"Uh, yes." I say in the most awkward way humanly possible.


We kiss each other quickly and I look down at my left hand, sporting a 2 carat solitaire that symbols Barbie officially found Ken.


We continue hovering over San Diego, and when it lands and the pilot can't hear me, I go, "um...is this a real ring or another non-real ring?"


He laughs that comforting laugh, pulls me close despite my obvious confusion, and says, "Yes, I want you to be my wifey."


Note: I wasn't excited at all in the helicopter. I was confused and wanted to ask him if this was real or if this was a declaration. It was only when we got back into his car, where he popped the glovebox and pulled out a mug that reads, "Does this mug make me look engaged?" when it clicked for me.


I'm getting married.


To my absolute best friend.

To the guy who can make hospitals and helicopters be extraordinary.

To the man who compares squirrels and acorns to the way his brain works.

To the man who challenged my conventional ways of thinking to later accept them as his own.

To my business partner, and partner in crime.





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