On January 29, 2011 I proposed to my girlfriend Ashley overlooking the Golden Gate Bridge and the city of San Francisco and invited all of my friends (and the internet) to watch as I did it. I love my fiancé Ashley. I also love the internet and social media. So, naturally, when it came time for me to propose to my girlfriend I decided to combine the two, and who doesn’t love hearing about (I think) creative ways of proposing? Here’s how it went down.
One week before the planned date my accomplice Lucas and I performed a reconnaissance mission to the planned location Hendrik Point on the Sausalito side of the Golden Gate Bridge. The weather was warm and sunny making for a picture perfect sunset across the Pacific’s horizon. Unfortunately, this weather would not remain through the week and would be replaced by cold rain and blustery wind. We tested the internet connection of our mobile hotspot and planned out each step I would take including the exact spot where I would drop the knee. After coming up with a few alternative scenarios just in case, we left, not to return for one week for go time.
That week, Lucas and I would meet after work and begin working on the specifics of the plan. First, we needed a platform where all the elements would live and where I could point everyone to go during the day. For that, we used a basic Tumblrtheme with a few custom modifications thanks to Lucas. I titled the site “Project:Proposal” and we began adding features.
Layout of the Tumblr site we created
At the top of the page we added a custom Google map that would be constantly updating our location throughout the day as we drove around San Francisco. Below that was a window for a slideshow of pictures that would automatically be updated as I took pictures using the Smug Mug iPhone app. Underneath the slideshow was a space for me to update the blog with status updates and/or videos. And finally, there was an embedded Ustream window which would be broadcasting the proposal live from the location in San Francisco. Once the day arrived I would use Hootsuite to schedule Twitter and Facebook posts throughout the day pointing everyone to the Tumblr page, which would also have an introduction video of me explaining the proposal plan.
You might be thinking to yourself “how did you insure that she wouldn’t get tipped off from her friends who had seen your status updates?”. This proved to be a challenge that almost became a deal breaker for the entire plan. Lucas and I brainstormed several different ways of getting ‘phone control’ as we called it. Ideas ranged from tricking her into forgetting it somewhere to straight up stealing it. We made an attempt the night before to cut off all the power to the place where she lived in hopes that her battery would be dead without enough time to charge it. This failed horribly and ended up just cutting the power to the rest of the house where she lived. We decided to take a drastic measure that Lucas brilliantly came up with. Knowing that Ashley’s mom was the account holder for her cell phone service, I called her and told her to call AT&T and temporarily ‘disable’ Ashley’s phone AND set a new password different than the main account password so Ashley wouldn’t be able to re-enable her phone.
The day finally arrived and I woke up to a HeyTell message from Ashley explaining that her phone wasn’t working. Excellent. With status updates locked and loaded, an iPad 3G tracking our location, and my iPhone ready to snap pictures, we left for San Francisco. Oh and I had the ring too. As I kept Ashley distracted window shopping and eating lunch, I anxiously looked at my watch as the time approached for the first status update to launch. Within five minutes of the first status going out I got a text message wishing me luck on my proposal. “Great” I thought, “I didn’t account for this”. Now I couldn’t let Ashley use my phone at the risk of someone sending me another text message or phone call. This wasn’t that easy because she constantly was asking for my phone in order to try and figure out the issue with her phone service. Using coded messages, Lucas kept me updated with the status of everything throughout the day. Things were, considering all the elements involved, going smoothly.
The time approached for us to cross the bridge and head up to ‘the spot’. I was sick to my stomach because I was so nervous. I told her I knew of this “cool spot” where you could see the whole city. After crossing the bridge and driving up the hill, I parked the car and, ever so carefully, hid the ring in my coat pocket. Unlike the week before when the weather was warm and calm, today was drizzly, windy, and cold. It took some convincing on my part to persuade Ashley to actually get out of the car into the blustery elements.
Ashley had no idea she would be engaged within 5 minutes
We walked up to the spot and out of the corner of my eye I could see Lucas and his girlfriend Amy in their positions quietly and inconspicuously following us with a video camera live streaming the whole thing (Lucas wore a hat and Amy wore a wig to guarantee Ashley wouldn’t notice them. I have dedicated friends). I carefully guided her along my predetermined route keeping her attention away from Lucas and Amy and then I had one last picture taken of us to be uploaded to the site.
We continued walking and landed on my mark. I told Ashley I had something to show her and brought out my phone and played a slideshow of pictures from our 1 year anniversary. After the slideshow was finished I turned Ashley towards me said my sweet nothings to her, reached into my pocket, got down on one knee and asked her to marry me. 
As you can see in the video, she was very, very, surprised and excited. And so was I, so much so, I forgot to put the ring actually on her finger and she asked me “aren’t you supposed to put the ring on?” and I responded “I don’t know, I’ve never done this before!”. After getting the ring on her finger and sharing some hugs and kisses I pointed over to where Lucas and Amy were positioned and they came out and handed Ashley roses and me a bottle of champagne.
Project:Proposal was a success and Ashley and I were officially engaged to be married! Once everyone watching was sure she, had in fact said ‘yes’, text messages started pouring in with congratulations and well-wishes (and also a few shout-out requests for the camera as it was still broadcasting live). I was excited everything went so smoothly AND she said yes! So excited, I shook up the champagne bottle and completely didn’t take into consideration the wind and exploded the champagne directly into a headwind all over myself and my new bride-to-be. It was a newbish move, but we had a good laugh (and so did everyone still watching live). That day, five months ago today, Ashley said “yes”, and one month from today, Ashley will say “I do”, and I cant wait.
Watch the recorded proposal video here
I a m C o l b y 