Personal Board Update: Engagement Story

Hi David,

For those who may not know yet, I proposed to Mikayla! And she said yes!

One of the issues with having such a brilliant girlfriend (now fiancée) is that I knew it would be hard to surprise her.

Before I get into the juicy engagement details: I met with Doctor Handsome a few weeks back for my quarterly check-in - still in remission!

Now, onto the engagement....

Mikayla gave me more creative freedom with the ring than she typically gives me with important decisions, so I needed to do a lot of research. We went ring shopping together back in May, and visited to a handful of ring places (jewelers?) to find the right one.

One of the hardest decisions I needed to make was where I wanted the side "kites" to be, which are these little diamonds on the sides of the ring.

I couldn't decide, so I had them make me graphics and print out the 3D designs to be extra sure. They were like: "Well we haven't sent over the CAD files before" and I was like "Well you can".

There were a lot of trade-offs - if I choose the middle one above (tapered band to fit the kites) it would mean the band would be little wider, so it would be difficult to stack rings next to each other.

Anyways, I decided on the "cathedral shoulders" for the kites.

There were a lot of other mini decisions along the way, but here's the end result!

As for surprising her, that was a whole other issue. She was already a bit skeptical that it was coming soon.

One reason she was skeptical is we both knew it "had" to happen soon.

To put it more directly, she told me a year ago: "You have 18 months. I don't want a long term boyfriend."

When you have an expiration date, it adds a healthy touch of urgency.

All that said, I knew I wanted to spend the rest of my life with Mikayla after like 7 months of being together. Once we got Tupperware around month 9, it sealed the deal.

Since our 3 year anniversary was coming up (from when we started dating), I told Mikayla: 'I'm going to take you on 3 weekend trips this fall to celebrate being together for 3 years."

If I was her, I'd think: "Oh! Maybe the engagement would happen on the first trip. Or maybe the last one?"

But no! It was going to happen on the 2nd weekend trip 😈 Impossible to guess.

The initial plan was to bring her to our favorite spot in the Catskills in upstate New York and propose to her on a mountain. We like hiking and my dad proposed to my mom on a mountain, so it felt right.

I was thinking I'd propose on this chairlift that runs on Windham Mountain.

There were two issues with this plan:

In the past year, they made the chairlift and mountain closed to the public. You had to be "members" of their fancy club. I tried to get around the rule, but no luck.

I was flying out Nes (one of Mikayla's closest friends) all the way from Texas to be there. And her flight was getting in 30 minutes too late to get to the mountain in time.

So, I planned to propose on the platform at Kaaterskill Falls.

Last year we went, it was pretty much empty, so I figured we'd have the platform to ourselves.

Naturally, there was a ton of traffic on the way there, and Mikayla says, "we really don't need to go, we'll have to walk like a mile because of how busy it is."

And I'm like: "No no, I really want to."

Then I get this concerning text: "Dave if you see this hold off"

I make an excuse to "call my boss about some work deal" so I could call Dave, Isa, and Nes who were secretly going to meet us there.

I said "I'll delay, just go right to the platform".

Naturally, the platform was crazy busy. Here's a photo I took from when we got close.

Mikayla doesn't like crowds, so this wasn't going to work.

We turn around and I'm just unsure what to do.

Then we walk over this other bridge, I look down, and see the perfect spot.

My "boss is blowing up my phone," so I tell Mikayla I'll meet her "up there". Once Mikayla's out of sight, I sprint to my friends to coordinate.

I tell them to look natural and stay out of sight.

Then I find Mikayla and say, "Hey let's go check out this bridge?"

I take Mikayla by the hand and lead her under the bridge. On the way, I see Dave, Isa, and Nes crossing the bridge above, looking very suspicious and unnatural.

Mikayla doesn't notice.

I turn Mikayla so her backs where they're supposed to be, and look over her shoulder to make sure they're capturing the moment. They're nowhere to be found. Completely out of sight. I'm like shit.

So Mikayla and I are awkwardly under this bridge, my friends aren't there, I'm sweating, Mikayla's like why are you being so weird.

I'm just like looking around trying to make small talk: "This is nice, beautiful bridge. Nice stream," as I search to see if they're hidden.

Then I'm looking at Mikayla and just start nervously laughing. Then she laughs back. We're looking at each other, awkwardly laughing. Mikayla knows something's up.

Then I say: "so we've been together 3 years, and I know I want to spend the rest of my life with you."

And then I get on a knee (I think my left knee?) and go: "will you marry me?"

She starts crying. Says "Well, yeah!"

I awkwardly open the ring case, end up opening it upside down.

I realize it's upside down.

She sees it and screams. I hear Dave, Isa, and Nes scurrying on over from behind the bushes.

And I'm like: "wait should I put it on?"

And she says: "Um yeah!!"

Then there's champagne and a blur.

We're engaged!

In case you're curious, here are a few far less significant (but still fun) moments from the past 3-4 months.

My brother Michael and I did a 527 mile bike trip from San Francisco to Los Angeles. Here's the youtube video if you want to check out the trip highlights.

My brother Sam and I went to the Oklahoma - Michigan game back in September.

Mikayla and I took my Dad and Mom to see Stephen Colbert for his last season. My Dad's been following Colbert for at least 15 years now. Thank you Joe Luongo for the tickets!

A few days ago I participated in an 8-mile skateboard race down Broadway. It's my first time joining the race since high school (raced all 4 years). I took this photo below that shows some of the chaos - someone falling in the middle, hundreds of riders running red lights. Most people have a helmet on though!

Hope you have a wonderful fall ahead.

Love,

David