Emily and Jordan

Emily's Proposal in San Ramon, California

How We Met

Jordan and I met two years ago through tinder, of all things, and instantly had an amazing connection! We spent the first 24 hours talking non-stop. We swapped embarrassing photos and videos, talked about our families, and eventually wrapped up the conversation by planning our first date. Jordan must have really liked me because she agreed to meet me in the middle of the woods, with my two very large and obnoxious dogs for the date. The moment Jordan stepped out of the car, and I got to see in her person for the first time, I knew instantly that she was incredible and I was in for one hell of a hike. I spent the entire three hours talking Jordan’s ear off, telling her crazy childhood stories, all about my hopes and dreams, everything about my friends and family…and by the time we finished the trail I realized I barely let her get in one word! My heart sank because I truly believed that I had messed things up and that this was the end of our time together. But to my surprise, before saying goodbye, she kissed me! And that was the end to my very last first-date.

From that moment on we were inseparable. We lived an hour apart for the first year of our relationship and then finally got to move into our first home together. And let me tell you, there is nothing more amazing and joyful than getting to fall asleep with the person you love every night and getting to wake up to their face first thing in the morning…well, unless the dogs snuck between us! I’ve known since the beginning that she was it, she was the one. And after a while, we started to discuss our future together. Now, you have to understand this proposal came as a HUGE shock to Jordan (you can probably see the confusion in her face the entire video) because every time we discussed marriage and proposals I told her that I really really wanted to be the one proposed to. I’m a huge romantic, and there is nothing more that I wanted in life than for someone to plan out an elaborate proposal, catch me super off guard and surprise me with the perfect ring.

I literally spend all of my free time watching proposal videos on YouTube and Facebook and spend hours, and I mean hours, sobbing on the couch. So the thought of that happening to me is all I ever dreamed of! So knowing all of this, what I am about to say may sound super weird and confusing and might not make a lot of sense…but one day (around Thanksgiving 2016) I heard me and Jordan’s song come on the radio, and all of sudden this amazing proposal idea popped into my head. For the rest of the day I could not shake the thought out of my mind. I could see it, clear as day! All of our friends and family gathered along a path, reading to Jordan something romantic, me waiting in a gazebo, asking her the ultimate question. And that’s when it dawned on me…I should be the one to ask! Jordan does everything for me. She takes care of me, loves me more than anyone, always puts my needs above her own. So I thought to myself “Why in the world wouldn’t I do this one amazing thing for her!?” So the planning began. After skyping her parents in California, and asking for not only their blessing but also their help…we started planning what would be (in my opinion) the most epic proposal ever.

How She Asked

Me, her friends, and especially her family spent 4 months planning the proposal. I knew from my initial vision of the big day that I wanted the most important people in our lives to share this incredible moment with us…but it turns out we have about 40 “most important people” in our lives. Which is nothing to complain about! How amazing is it that we have THAT amount of people loving us? The only down side to having so many incredible people in our lives is now 40 people have to keep a HUGE secret! Having that many people involved made me extremely nervous that she would figure it out before the moment came. I just kept thinking to myself that someone is going to slip up or accidentally message her about plans. But to my surprise, and hers, she had no idea!! Her mother and aunt Pam were seriously the backbone of the operation. Being in Virginia and knowing I wanted to propose in California (where she grew up and the place she loves most) it was difficult to find the perfect venue, ship decorations, and talk to vendors about the after party. But her mother and aunt came to my rescue. They spent about a month traveling around Jordan’s hometown trying to find the perfect place with a path, some type of water, and a gazebo. And they sure did nail it! They helped me find the proposal location, helped me coordinate with everyone on the west coast, and also found a location for us to party at afterwards! If all of that wasn’t stressful enough for them, my next task for them was to find an excuse to get Jordan out to California. She had been telling me since Thanksgiving that she wanted to go home for spring break in March. So I figured that was my opportunity to surprise her! It took her family weeks to finally get a confirmation from her that she was indeed going to go home. It drove us nuts. Obviously she had no idea that it was super important she pick and confirm a date quickly, but I had at least 15 people that were flying in for this and needed hotels…and the longer she took to decide the more antsy me and everyone else were getting! And once we finally did get a solid plan out of her, about a month before the proposal was to take place she spent an entire evening crying to me about how she might have to cancel her trip home because she’s too overwhelmed with school (she’s in a rigorous PhD program). I can’t tell you how hard it is to comfort someone else when you’re screaming internally. Thankfully, after some chocolate and snuggles she felt much better and decided going home would be good mental health break for her! Whew! I dropped her at the airport on Monday, told her I was going to travel 2 hours south to spend the week with my parents and kissed her goodbye. Three days later I hopped on a plane with my family and friends and the adrenaline kicked in and didn’t stop until the moment she said “yes.”

Here’s how the proposal went down: Two weeks prior to her arrival in Cali, her parents told her that on the evening of the 18th her and her brother Blake would be meeting their cousins in this neighborhood to take family photos. This was our cover story to get her all dressed up and to keep her void of suspicion while driving to this unfamiliar location. Once she arrived, she got out of the car to find her mom and dad standing in front of this path (blocked from view thanks to some tall hedges) holding a box with a big bow on top and tag reading “From Emily, To Jordan.” She was very confused because her mom and dad were not supposed to be there…but opened the box without much hesitation. Inside the box was an iPad with a video of me pulled up on it. When she pressed the play button she watched a short video of me saying something along the lines of, “Hey babe, I know you must be super confused right now because you’ve been thinking all day that you were getting ready for a cousin photoshoot…but I have something just a little different planned for you tonight. As you know, our two year anniversary is in a few days and I wanted give you an extra special gift. But, you made me promise no gifts this year…so instead of a gift I’m going to tell you a love story…my favorite love story in fact! But since I can’t be there to tell it to you myself, I’ve asked some family and friends to come help read it to you! So take your mom and dad’s arms, walk with them, listen carefully and above everything else…remember I love you more than you could ever know!”

Her mom and dad and brother lead her through the very narrow entrance to the winding path where she saw 6 large groups of people holding up “chapter” signs. The signs were huge so it was hard to tell who was standing behind each one. Chapter 1: High school friends Chapter 2: Her family (aunts, uncles, cousins) Chapter 3: The family I nanny for (which consists of two little boys and their mom-who I consider to be my little brothers and second mom) Chapter 4: My best friends Chapter 5: My family Chapter 6: Her best friends Her mom and dad walked arm and arm with her to each group, with her brother following closely behind.

Each group she got to would drop the sign, revealing who was behind it, and each person would read to her a portion of our love story. They recounted to her how we met, how we fell in love, how we made it through tricky times, and the very last group told her all about how much I am over-the-moon in love with her. (She told me later that she figured out I was proposing when she got to the family I nanny for. They live in Virginia, so it was easy to figure out that them being in California meant this must be something way more important than an anniversary gift) The last person, her best friend, ended the story with, “But that’s not the end of their story, they’re just moving on to the next chapter of their lives.” Her family led her around one last turn in the path where she was brought to the bottom of a staircase that led up to this decorated gazebo where I was waiting. The moment she saw me standing there she sprinted up the steps as fast as she could. My heart melted in this moment and it was hard for me to catch my breath.

Once we were in each other’s arms she held on to me for a lifetime just saying over and over again “I can’t believe you did this!” Once she was able to let go, I told her again about how much I love her and I have known I’ve loved her from the moment I saw her. How I want to spend the rest of my life with her, and how I don’t want to go another day without being married to her. I got down on one knee, asked if she would marry me and thankfully she didn’t hesitate even for a moment. It’s actually quite funny watching the video because most girls, when asked the question, put their hands to their faces or stick out their hand so the person proposing can put the ring on it. But not Jordan!

She pulled that ring out of the box so quickly and put it on her own hand, haha! I loved it! She knew what she wanted and wasn’t hesitating in the slightest! After she said yes the rest of the crowd came to join us in the gazebo. After looking at the ring and hugging and laughing about details of the proposal all 42 of us drove down the road to this clubhouse in the hills. We all ate and drank and spent time together taking lots of pictures and enjoying everyone’s company. It was amazing and went off without a hitch! The perfect evening!

Our Video

Watch more proposal videos & follow @HowHeAsked on Instagram for more stories!

Special Thanks