Mario Sundar's Speakeasy

Spero Ventures. Early LinkedIn, Twitter. These are my thoughts on tech, brand, marketing and community.

Love in the Time of Covid: A Valentine’s Day Story!

How does one go from “Panic Room” to Getting Engaged in 365 Days?!

“It has surface innocence, surprise, the revelation of a concealed meaning, and the catharsis of solution.” – Stephen Sondheim

A year ago, I had spent 365 days not seeing a human soul for 365 days, thanks COVID!

Here’s how I pulled off a surprise proposal between then and now!

Yes, what a difference a year does make… some years, they do!

That said, I stumbled upon a lot of highs and lows through this process of planning a proposal (how does one find a ring to her liking, plan a surprise, what elements should it include) and figured I’d write this down, both for my own sake; and all you gentlemen & women, who might find this interesting.

There’s only one rule while building a proposal: Surprise, and surprise, and surprise. With a final reveal. And, one more thing…

All of Life’s a Play.

“All the world’s a stage, and all the men and women merely players: they have their exits and their entrances; and one man in his time plays many parts, his acts being seven ages.” – Shakespeare

A proposal, like Life itself, is kinda like a stage play… with an audience of one. Obviously, you know your audience, so use that intel for all the surprise one can glean.


Step 1: Start with the End in Sight


For the longest time, I had no clue how, when & where I was gunna do to propose. All I knew is I didn’t want it to be in public, cos it sounded cliched.

So, I’m driving on the Golden Gate Bridge (back from the jewelers 1 ) and it hit me.

It had to be home. For us.

It doesn’t matter “when,” but the “where” is home. Once you got the “where,” everything else works backward from there.

And, it had to be around family. Our very first date, we talked about our families, me (as an immigrant) about how I missed mine, and hers (as someone very close to a large family) about how much it mattered to her. And knowing how she felt about her family, it had to happen around them, and a dear friend of mine.

Once you have the end in sight 2, it’s easy to plan.

I love the idea of bringing it back home, for a couple of reasons:

  • For starters, it’s the best surprise possible. Creating a ruse, is a breeze, since planning a weekend away, makes that the “where” for her.
  • The longer you plan the “weekend,” the bigger the surprise when you return home.

She will not enjoy those 24 hours, but she will, the return home, once it all sinks in.

Guaranteed.


Step 2: Stage The Ruse


Now, for the fun part.

The keys to a surprise, whether it’s a magic trick or a movie script is one thing only:

Misdirection.

Storytelling (whether it’s in movies – see Ocean’s 12 – most profoundly in magic) is about setting up an elaborate ruse and ensuring your audience is staring deeply at that ruse, certain that the rabbit (or in this case, engagement ring) is gunna come out of the hat they’re looking at.

Setting up that ruse, the hat they stare at, is pretty much the entire job.

For me, it came together, when I got a Friday off (serendipitous) and decided it was going to be the ruse. I had planted enough hints along the way (at very normal moments, mind you) that I wanted to take her to my favorite town in all of wine-country – Yountville – and you definitely wanna play that up.

The key is to double-down on (in this case) the wine country trip, as much as possible. I, quite literally, planned an afternoon at Clos Pegase, dinner at my favorite restaurant in Yountville, and brunch the day-after in Bouchon, and a massage (!); all of which bear the hallmarks of a proposal.

And, you wanna act coy, while playing it up. Also, this wasn’t a last-minute addition, we had been planning a trip to wine country for some time. So, it felt very natural (to her) that I’d propose there. 3


Step 3: Let There be Music!


It is commonplace to see a photographer or two jump out of the bushes to photograph an unsuspecting fiancé, when she has said the magic word — Yes — and yes, I’d highly recommend that, especially if you’re planning a surprise for the ages.

But, what’s more important, and it was to us, was music. Our music.

I knew her family (especially her Dad) were big fans of the Beatles, and I can’t stop thinking about  wisdom from Dylan (no matter the occasion). So, I put together a playlist, and stumbled upon an Octoberfest event the day after I planned to propose; so I reached out to the musician.

Through Tim, I found a journeyman musician, Dore (a neighbor almost) who was more than thrilled to make our playlist real.4

To wit: the music was truly what made that evening special, and filled with happy tears.

Always, go with the music. Here’s my playlist that I can’t believed we were able to pull off for that moment. I had them arranged by chronological emotions (from start to finish) and Dore picked the ones he was most comfortable with.


Step 4: Surf the highs-and-lows


The key to any act of storytelling is relentless surprise.

Quite literally, that’s all it requires, and once you’ve decided to take her on a journey (until you return to home), the entire path is paved with surprises.

All you have to do is tension and release and surprise. Keep it tightly wound, and any pratfalls and unintended bloopers along the way only adds to the elements of surprise. That’s the most important thing you can do when you’re building a score (or a scare) or a proposal.

“You’re playing with tension and release, and surprise. When do I sit in the moment, and when do I explode a moment. When is the audience ahead of me? Keep surprising us. That’s the most important thing you can do when building a score.” — Lin Manuel Miranda 5

When is the audience ahead of me?

There were a couple of moments, where I thought the game was up.

For starters, the first winery, I’d called ahead and asked them if anyone had proposed there and asked them to basically give us the same deal.

That said, their service left a lot to be desired, we were hounded by hornets, and it was kind of a cluster.

While driving to our dinner at Yountville, my calendar which was usually synced to the Apple Carplay popped up a calendar event that I had shared with the folks who were in on the surprise, and were gunna be waiting for us home! Spoiler Alert: she didn’t notice it, but I assumed she had seen it?!

Unsure of what to do, and unable to ask her, I had to preemptively distract by asking her straight out if she expected a proposal during the trip?!

Well, I had to…

And, when she said “Yes,” I blamed the winery (who kinda messed up big time) to suggest I wanted a perfect proposal, and the hornets kinda ruined it.

Next day, I find the best seats in Bouchon (of course, that was planned ahead of time too), to intrigue her too, and yes, she thought I was going to propose there too.

Fast forward to home, it was so worth it. And, it’ll be tough in the moment to hold it in, but remember, this is what makes that finale oh, so delicious. Just popping the question, giving a ring, and photographers jumping out ain’t as sweet.


Step 5: One More Thing — What begins with family, ends at home!


The One More Thing, for us was always going to be family. It was the thing and the one-more-thing. And I knew, once the surprise to see the photographers and the musician sunk in, seeing family (hiding in the other corner of our patio) was the piece-de-resistance.

And, boy, it was.

The principle of storytelling, the third act has to tie somehow to the beginning of what started it all in this world.

The Closing Image can be a single scene or a series of scenes, but the mirror effect between Act I and III works best if you dedicate an equal amount of screen-time for opening and closing images. — Three Act Structure in Screenwriting 6

It is but natural, that our first conversation, centered around home & family, would tie back to proposing in front of that very home & family. Nothing else made sense to me in the grand scheme of things.

“Your finale has ups and downs and isn’t a straightforward race to the finish line.”

Once you spark Point B, the rest is putting together a roller-coaster to Point B.

My goal was always to propose at our home, and I knew wine country would be the perfect ruse. And, yes, you can’t make an omelette without breaking a few eggs (and, smiles) along the way; but, what really matters is the finale, the conclusion, the rock on which you’re building your (both you and her) future.

To be honest, finding love in a pandemic, is like finding a needle in a haystack (but just with one more thing, the haystack’s on fire), but when you do, the feeling of elation is a high, higher than usual. The job now is to keep that flame alive (not the haystack, but in our lives).

All’s well that ends well.


Outro: “The Man in Me”


You didn’t think I’d end this post without the words of my favorite poet. Of course, there’s a Dylan song to capture this moment as well.

Stumbled upon this gem, yesterday while writing and it immediately spoke to what finding love might feel like. And I don’t mean love in a cheesy way.

Happy Valentine’s Day to all you lovebirds out there!

"Storm clouds are raging all around my door
I think to myself I might not take it any more
Take a woman like your kind
To find the man in me

The man in me will hide sometimes to keep from bein' seen
But that's just because he doesn't wanna turn into some machine
It take a woman like you
To get through to the man in me." 

    — Bob Dylan, New Morning "The Man in Me." 


  1. long story. But finding the jewelers was a nightmare, in and of itself. But, I’d alway recommend going to the craftsmen and women vs. the major stores that are sleazy to say the least. I did find our jeweler after visiting 4 or 5, through a cursory google search, in San Francisco. ↩︎
  2. I think will do it at home kind of like how we were discussing at the jewelry store. And I’d love to have a live jazz band and would love to have a surprise thrown in when I take her to Healdsburg and then when we return will have the whole place set up, and I could also get the patio cleaned out that we needed to clean right before that time. ↩︎
  3. I feel bad as I describe this, and those 24 hours were torture to me, not that I was bumming her out, but to hold the secret in, so I could ensure the big finale surprise as best as can be! It was a thrilling 24-hours! ↩︎
  4. If anyone reading this is interested in a musician for their special day, reach out to me, and I’m happy to connect you to Dore. ↩︎
  5. Lin Manuel is talking about the elements to build a musical (which is similar to a stage play) ↩︎
  6. I love the movies that get this right, and if you’re writing your proposal, it’s essential that your third act, ties to the first. Innumerable films nail the landing, including Soderbergh’s Kimi that just launched on HBO. Without giving away much, the final scene is a direct resolution, denouement from Scene A that kicks off the movie. ↩︎

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2 Responses

  1. josephkam says:

    Loved reading about this very special time in your life, Mario. Congrats to you both!

    Liked by 1 person

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