How a Social Media Nerd Proposes to his Girlfriend

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

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Tacking to Complete Goals

I consider myself to be a “goal setter”. I set a lot of goals for myself in order to be more productive and complete the tasks I think are worth putting forth time and effort. Being of the goal setting type, I always have enjoyed hearing or reading about how other people accomplish their goals and what “tactics” they use in order to accomplish their goals. I think that setting goals can be a great practice for accomplishing tasks that are important to you and a great way of getting things done. Not everybody is a goal setter, but for those of us that enjoy setting goals, here is what I do.

I had set an aggressive goal in July to have purchased a house by September 1^st of this year. While that goal was lofty, it was still very much achievable. As I said in my earlier post, I am currently unemployed and pursuing real estate investing in order to make the most of my time without a job. While trying to complete my goal of purchasing a house (or any goal for that matter) I ask myself one question several times a day:

“What can I be doing right now to be more productive and get closer to achieving my goal?”

Asking myself this question keeps me focused on the goal I have set and helps me determine the steps necessary to get closer to achieving that goal. This question also helps me break my goal into sections and forces me to think of what can be accomplished next. I like to break my goals into these sections because it takes away the feeling of being overwhelmed by a huge goal and keeps me focused on my set main goal.

Buying a house, for example, can seem slightly overwhelming when looking at the big picture. However, there are many smaller steps in-between where you are now and buying a house. One of my professors once used a great analogy between accomplishing goals and sailing. Let me explain. In sailing, you don’t go straight from point A to point Z in a straight line. Instead, you tack. You make many turns and go from point A to B, B to C, C to D, and so on until you reach your destination of point Z. The same is true with completing your goals. You have to “tack” and go through the necessary steps in between you and your final destination (or goal). With every turn of the boat you are moving forward towards your desired goal. Also, you always want to have your focus set on where you ultimately want to end up and through determination and “tacking” you will arrive at your goal. So, in my example of buying a house, it could look like this: Where I am now is point A and purchasing the house is point Z. One of my first “tacks” could be determining how much money I can invest, point B. Point C could be finding a real estate agent. Point D could be touring a house. These “tacks” continue all the way until you have reached your goal of buying a house. Now, I’m not saying it only takes twenty-six “tacks” to buy a house (could be much, much more) but, it illustrates my point. Thinking about how you can “tack” towards your goal can be really helpful as you determine the steps necessary to get there.

Also important, is the timing factor of goals. There are some goals that have a constraint of time and require a due date to be put into place such as turning in an assignment for school or your taxes, for example. I think setting due dates for all your goals is important because it adds some pressure and keeps you moving towards completing your goal. That said, what happens when you don’t achieve your goal by the time you had planned for? This just happened to me when I had not accomplished my goal of purchasing a house by September 1^st. While this can be very frustrating and discouraging, what you do after the deadline has passed is more important than the due date. I knew I wanted to still pursue real estate investing, so I had to take a step back and re-examine my goal, and make a new timeline for my goal. I also had to ask myself “is this goal still worth pursuing?” The answer was yes, so I had to press forward, and continue tacking towards my goal. This takes tenacity and perseverance (two things I am actively working on) in order to continue towards your goal.

I hope after reading this you can set some goals that are important to you and that the analogy of tacking has helped you view accomplishing your goals as more manageable and less overwhelming. Now, go set some goals and be productive!