By now you've probably heard some version of this story from one or both of us, but I think it really does come best from Tom:

In summary, the proposal was so much planning--MONTHS of planning--cast to the wind and leaving me with nothing but wild uncertainty, and off the cuff winging it.  Totally not a heart-stopping stressful experience, not at all.

THE BACKSTORY

Backing up a few months.  Caitlin and I had long been discussing our future together.  I had long decided in my mind that it would be a cute idea to propose on our 1 year anniversary.  I wanted to get a ring fairly early, just to have it on hand as extra motivation to really dive into planning this incredible proposal that would blow all other proposals out of the water.  I had already had long conversations with Caitlin about what kind of ring she would want early on in our relationship.  So I consolidated my pages of notes on the perfect ring, reread the 4 C’s of diamond shopping, and went to a jeweler in early March.  Hours later, I walked out of that jeweler having purchased the central diamond for Caitlin’s engagement ring.  Over the course of March and April, the rest of the ring was picked out, and in early May I had the ring.

I had always planned on singing something to Caitlin when I was going to do this amazing proposal presentation.  Somewhere in talking about proposals, though, Caitlin had mentioned that she would rather have a CD to listen to on her own time.  That way she could listen with her full attention, rather than have to sit through a whole song knowing that the proposal was coming, and being unable to concentrate on anything happening at that moment.  So I decided to record a song for her.  I had decided that to make it all the more special I would get a custom made USB to put the recording on, so it would be something unique, just for her.  I spent weeks putting together lyrics written about why I love her, and a majority of a week’s vacation was spent recording on my computer in the guest room of my condo.  I wrote a speech to give to her as well, intending to also say it at this super amazing, well planned, surprise proposal.

Caitlin wanted to be proposed to in a secluded, pretty, outdoor place.  Hopefully with a photographer hiding somewhere in the bushes ready to stealthfully take some amazing reaction shots, for when I blew her away with this amazingly coordinated surprise proposal event.  I contacted a few photographers, and had lined someone up who was ready to be on call for either the 3rd or 4th of July, which I presumed would be one of the days in which I would propose to Caitlin.  Caitlin wanted to be surprised by the proposal, and this was the big challenge.  I had talked to the photographer and he assured me he would be a photo ninja.  So the task of keeping the surprise would fall on me to not blow my cover before proposing.

PROPOSAL FAIL

We made plans to go to Grape Island on the 4th of July.  This was going to be so perfect.  Everything was in order, I had all my materials, I was ready.  Then, hurricane.  WEATHER, WHY MUST YOU TORMENT ME????  We cancel our plans to get together, and spend the day I was planning for months, MONTHS, to propose to Caitlin, apart from one another.  I spent most of the day trying to convince Caitlin that we should rain check for the next day, which eventually panned out.  We had soft plans to redo this on July 5th.

THE PROPOSAL

Here we are, the day after my incredible proposal plan was supposed to have occurred.  I no longer had a photographer, but everything else is still intact.  I am on edge, having missed the opportunity that I had so long been planning for, because weather decided not to cooperate with me.  Preparing to do one of the most nerve-wracking things on the fly is not easy.  I slept about 5 hours the night before due to mental panic.  I woke up and packed a gargantuan backpack of lunch things for the trip as an excuse to have my backpack and to conceal the ring box.  Whoever designed ring boxes certainly did not have proposal stealth in mind.  As far as I know, Caitlin is still unawares of my plans to propose, so I do have that going for me.

I go to pick up Caitlin, bringing my huge backpack and a large wrapped painting as an attempted birthday gift, turned anniversary gift with me.  This worked out as a nice diversion from the proposal, as Caitlin took this to be a big enough surprise for one day.

We eventually get to Grape Island and hiked along the trail.  I had read up on the island and found that it had some nice views of Boston that I had in mind as possible locations to propose.  I was now wildly nervous because I was completely winging this proposal.  I had no game plan, I had no idea what I would be doing, I just knew it was going to happen in the next hour that we were on this island.  I had a ring in my backpack and would not leave this island with it still on my person.  We eventually came to a clearing in the trees and there was the Boston skyline in the distance.  This is the spot!  I suggest we have some lunch here, so I can distract Caitlin with food and disguise my digging out the ring from my backpack with pulling out food.  I hand her some food and start to blindly retrieve the ring from the ring box.  I finally get it and am about to pull it out and do this proposal, when I notice in my peripheral vision that Caitlin is no longer sitting next to me, but is standing at the trail waiting for me to follow her.  “Where are you going?” “Oh, I’m ready to keep moving now.”  I pocket the ring.  Sigh, attempt 1….fail.

We later come upon a beach front.  Somehow our conversation organically moved to discussing what our wedding colors would be.  I am utilizing all of my will power to contain my nerves here and act as though this is totally normal.  I convince myself this is a good conversation because it will eventually just lead to the proposal.  We venture out to this sand bar peninsula.  Caitlin has made mention how this is her favorite part of beaches several times now.  “Oh, this is perfect,” I think. “I’ll propose to her here in this cool spot that we’ve been hanging around in for a little bit”.  I turn around and once again, she is already on the move.  I’m approaching a nervous breakdown, but hold it together externally, for appearances.  Attempt 2…..fail.

We’re talking about heading back for the ferry soon.  I’m panicking and hoping we encounter another good site in the next few minutes.  We stumble upon another beach with an unobstructed view of the downtown Boston skyline.  PERFECT! It’s a huge open beach, all to ourselves.  Caitlin notices the time and says we need to head back.  It’s now or never, I have to get this proposal in.  I say, “Wait,” and I grab her.  “First I have a question.”  I drop to one knee and pull the ring out of my pocket.  My rehearsed speech, all form of presentation, completely gone.  Seemingly apropos of nothing I say, “Will you marry me?” and Caitlin immediately said, “Yes”.  And the ring was on her finger and we were both just in shock.  “Wait, what? Did that just happen?” Caitlin asked.  I TOTALLY SURPRISED HER, I CAN’T BELIEVE IT!!! YESSSSSSSS!!!!!! “We have to go catch the ferry now,” she said.  And we ran back to the ferry.  I am now completely brain dead, engaged and ecstatic and have never felt so happy and incredibly brain dead.

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