Significant life events excite everyone, especially when you create a deadline for one. The preparation and anticipation leading up to the deadline motivate you to put your head down and do whatever it takes to pull off the memorable event. My recent self-imposed deadline happened when I proposed to my ex-girlfriend; who is now my fiancée! Just like any other big task that needs addressing, planning a proposal proved challenging which tested me to problem-solve on the fly as well as handle my enthusiasm secretly so I didn’t spoil the surprise.

Once you are either planning your own proposal or preparing for a significant task with a self-applied deadline, try to remember these points.

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Stay Loyal to Your Goal

• What are you trying to accomplish?

My girlfriend and I started to heat up our marriage conversations and we understood that committing our partnership was our next step. This is when I started to plan how to propose. The most important goal for this event was to create a memorable, genuine, and touching way to propose. For us, the extravagant public proposals – flash mobs and jumbotrons – didn’t fit our style so researching on YouTube! didn’t help.

Google had too many ideas so I didn’t put the pressure on myself to think of the perfect proposal right away. I rather just let my excitement participate in the back of my mind and wait for that “A-ha” moment.

Recognize Good Ideas

• Build momentum when there’s confidence.

While glancing through my LinkedIn homepage, I noticed a college friend’s job update. I noted his new company and never heard of it. I went to their website and then, “A-ha!” My excitement immediately resurfaced to the forefront of my mind and I began to craft this project.

The product that I chose allows you to customize a hardcover book by inputting photos as well as text boxes to create your own masterpiece. My book consisted of numerous pictures and stories from our partnership and I also added a bunch of blank pages in the middle with the intention to glue them together so we could cut out a shape. My goal was to place the ring in the shape that she’ll discover while reading through.

While constructing this book on the website, I noticed that in order to make this project better, I needed to get pictures that weren’t in my possession. In order to keep up this momentum, I needed to ask her parents for help.

(say to yourself in a suspenseful voice)

Recruit Cheerleaders

• Kind gestures go a long way.

Nowadays, traditional values mean more than ever. Personal relationships molded into online beings boasting highlight reels and email newsletters. Real connections are what matter most and need to be preserved through effort. As a sentimentalist, I found it important to include my girlfriend’s and my family with this significant life-event since we’re both family oriented.

1. I spoke to my family, parents and my sister, about my intentions to ask for my girlfriend’s hand in marriage. My mother offered a family heirloom, my great-grandmothers ring. This gesture meant so much and allowed me to plan the perfect proposal that included my family’s history.

I had the ring, but I still needed the blessings from my girlfriend’s families.

2. First up: her father and step-mother. This came a little unexpected but the conversation grew organically between us three and allowed us all to give happy hugs. Once the blessings were given, I asked them to help by sharing some pictures to include in the book as well as approval to speak to their parents.

My girlfriend’s grandparents are jewelers and I noticed that my family ring was smaller than a ring that she wears. I needed to get the ring adjusted to ensure it would fit.

3. I took the two rings over to her grandparents’ house and we all exchanged excited hugs. We started to go over how to mold the ring to her size. At the same time, I clued them into my plan and asked for them to participate. My fiancée started to ring shop with them to find the ring that she desired. I told her that I couldn’t propose until she picked out a ring. This also clued me into how serious she was with this decision. I consider myself a risk taker but I wanted to manage the risk in this situation. Her grandparents helped her find a ring while keeping my family ring a secret, knowing that I was going to surprise her.

4. Last up, her mother. Since she lives in another state, I had to settle for a phone conversation. We had a nice chat that ended in her delight to see her daughter and I continue our loving partnership.

Including all of these individuals allowed me to feel the love and support from the people closest to us. Their enthusiasm, excitement, and smiles acted like cheerleaders to keep me pursuing the perfect proposal with full confidence.

Accept Weaknesses

• Trust your gut when it tells you to ask for help.

Once the book arrived, the ring was sized, and the arts and crafts supplies were purchased, I came to a thought, “I have no idea what I’m doing.” Even during my Kindergarten years, I knew my future wasn’t in arts and crafts. I had a beautiful memento in my possession and I knew that my “bull-in-a-china-shop” hands would disgrace this hardcover book. Thank goodness for friends.

Two of my closest girlfriends were willing to help and I couldn’t have been more thrilled. We all sat down (when I told my girlfriend that I was playing tennis) and we all started to work on the book together. I began by doing the grunt work and we all enjoyed the project. Once an artistic hand was needed, my friend generously pushed me aside to make it pretty. Phew. That helped me immensely and as you can see, the finished product turned out great!

Roll with the Punches

• Handle challenges diligently rather than obsess over them.

When you create a plan, the universe laughs. My plan included numerous set-backs. Due to the approaching deadline, I didn’t fret about these obstacles but just quickly problem-solved to overcome them.

1. The family ring was the perfect size to begin with and we molded it to be bigger because I didn’t realize that the right-hand ring finger is always bigger than the left’s. You might ask: Why didn’t I know this? Oh yeah, because I’m a novice to jewelry.

• I had to redeliver the ring and her grandparents molded it back to its original size.

2. I ordered the book with the intention to propose on a certain Friday. “Thank you for your order. Your order will arrive” a week later than my intended proposal date.

• Okay, scratch that date. A week later is better anyways.

3. My friends and I crafted the book with a great solution to get the ring in the cut-out heart. After all the effort to preserve the ribbon that was going to hold the ring, I cut it causing us to find a new solution.

• We brainstormed a different approach and the finished product turned-out so much better.

4. Right before we started the proposal, my girlfriend asked, “Can we have a serious talk?” I replied, “Of course, are you having second thoughts about us?” (Thump, thump… thump, thump.) She said, “No, this has nothing to do with us.”

• Phew. We had the conversation and I knew that I could continue with the plan.

Remember to Relax and Have Fun

• When things get hectic, remember why you pursued the goal.

That morning, I entered my office and asked my boss, who knew it was the planned date, “How long do you need me here today? I can’t concentrate.” He courteously let me leave early so my girlfriend and I could start our drive to Aspen. We had to do some errands up there this certain weekend so it was seen as a burdensome trip in her mind; in my mind, it was a trip of a lifetime.

We drove separate cars which allowed me to find peace in my own thoughts and distance myself from nervous conversations. Listening to an audio-book allowed me to relax before this momentous occasion.

When we arrived in Aspen, I asked two great friends to help me stage a surprise proposal. We were in touch before my girlfriend and I arrived. My friends came over for a “catch-up” beer and I stashed the book in a predetermined location for them to pick up without her knowing. They then staged a scene in the closest park’s gazebo. They left us because they had “previous plans” at a specific time and then my girlfriend and I would leave exactly fifteen minutes later to play fetch with Bogie in the park.

Of course, right when they left us, my girlfriend wanted to go to the park right away. “Hold on, babe. I need to write some emails.” I then went to my IPad and typed nonsense to look like I was being productive.

Game Time!

Walking my girlfriend and Bogie to the park was one of the happiest walks of my entire life. I couldn’t stop thinking, “She has no idea!” We entered the park and threw the ball once for Bogie where I directly walked her to the gazebo in the middle of the park. She looked at the gazebo and saw a lovely bouquet of flowers and a hardcover book resting on the bench.

We sat down and read through the book together. Half-way through the book, my body position shifted to go down on one knee where she turned the page and saw the ring in the book. I said a few words that ended in a particular question and her next response was, “Yes!” A kiss followed, turning us into each other’s fiancée and fiancé, and we then finished the book.

I screamed, “She said yes!” My two friends came running out congratulating us with hugs, hand-shakes, pictures (I mean, look at these pictures! Thank you!), and a champagne toast.

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Truly Grateful
This special occasion marks an amazing moment for my fiancée and me. A touching addition to our commitment is the fact that there were so many people ready to support.

To my family, her family, my Denver friends, my colleagues, and my Aspen friends: Thank you to all of you for your generous contributions and support. Together, we pulled off the perfect surprise proposal, and she said, “Yes!”