How I Asked: Jess is a very smart girl and she’s good at figuring things out, especially surprises. I didn’t want a typical surprise proposal—I wanted it to be special in our own way, so I made it very apparent and sentimental.
Finding a time to propose was difficult, as things were always coming up at the last minute for Jess. So I decided it would have to happen on the same day she drove to Bothell, Washington for a work training. Jess really wanted to be with me before she had to make the three-hour drive, but I told her it wasn’t going to be possible because I got called into work. The truth was, I wasn’t working. I was planning an elaborate all-day proposal for her.
I sent her a video message that morning telling her that she had a gift waiting on her doorstep and her friends would be joining her for an all-day girl hangout so she wouldn’t have to be alone. I talked to her two best friends previously, so they were in on the proposal. Inside the package was a cast-iron tea set, pot, saucers and cups. Jess loves tea. The box also contained a letter with a riddle, and the riddle was the first clue for a scavenger hunt.
Jess and I had some very sentimental places around town where we’d experienced deep connections. Whether it was the location of a conversation, a kiss or just a moment of vulnerability with one another, we have markers all over town that were created in our hearts and minds. I wanted to use these locations for my proposal:
1. Ristretto Roasters: The first clue led her to a coffee shop we went to when we first started talking. I didn’t know at the time that she didn’t drink coffee! I had one of Jess’ friends waiting there to present the next clue in a coffee bag that had been emptied and refilled with tea.
2. Arlene Schnitzer Hall: Right after we met, I was gifted tickets to the Oregon Symphony by a family friend, and I decided to make that my official first date with Jess. On the day of the proposal, Jess showed up to the Arlene Schnitzer Hall downtown and was presented with the third clue—a box with the original tickets and the next clue.
3. Coffee Time: I then sent Jess to Coffee Time. There she was presented with another box containing a few select notes to remind her of the very deep and rich conversations we’d had there, as well as the next clue.
4. Le Happy: Jess’ next destination was a little creperie where we had some of the most vulnerable conversations while we were dating. Le Happy is also known for their board games, and we often played Connect Four and Sequence over crepes. Her final box was presented by her brothers and mom, and the contents included a couple of playing cards, pieces from the games we played and the final clue.
5. Broadway Bridge: We often crossed the Broadway Bridge on our way downtown for dates, so I figured the setting would be perfect for the proposal. The last clue led Jess there, where I was hiding, along with all of her family and friends. She walked out, looking excited and confused, but continued until she got closer to the center. I stood there waiting and popped out to surprise her. We laughed and cried a little and then I got down on one knee and asked her to spend the rest of her life with me.
That is our story, and we think it’s a great one.
The Proposal Story from Jess’ Perspective:
how they asked: It was September 20th, 2012. I woke up to a video from my boyfriend, Jeff, saying how much he loved me and that he had a full day planned for me to go out with the girls. Outside my door was a gift and the first clue for a day-long scavenger hunt he had set up for me. In my heart, I wanted to think it was the day he’d propose, but I kept telling myself, “No, he’s working all day.” He worked for AT&T at the time and it was the huge iPhone launch day, which nobody gets off. So I pushed the thought aside and continued on to my first clue. Each clue was handwritten in a poetic riddle that lead me to a special place where I’d find a familiar face.
The first place was a coffee spot where we had our first hangout together. He loves coffee and didn’t know I only drank tea, so it has been a joke with us since that day. I saw one of my best friends there with a coffee bag containing the next clue. Each place I went that day, I found my closest friends and family waiting to greet me with a uniquely planned-out gift and clue, which eventually led me all the way to the Broadway Bridge in Portland. We have a strange love for bridges, so it was perfect.
I remember walking up the stairs to the side of the bridge and seeing nobody there. I was confused, excited and had so much anticipation. My friend, Ange, who was with me for the whole day, encouraged me to keep walking until I saw someone, so I did. She lingered back as I continued down the path, and sure enough, hiding behind one of the pillars was my love, Jeff. When we saw each other, I started to laugh nervously and he started to cry.
I hugged him and then he brought me over to the side and explained how I am the surprise of his life. He told me how much he cherished me, not just as the one he loved, but as his best friend. As he was finishing up with those words, he got down on one knee and asked the life-changing question: “Will you be mine for the rest of our lives?”
Still laughing and now crying too, I replied with a “YES!!” Then, as he stood up to hug and kiss me, I saw my family and friends jump out to join our celebration.
How He Selected the Ring:
Jess and I always joke about being old souls, but we truly feel that way. We enjoy traditional things, though we are never ones to discredit new things either. We had talked about wedding stuff before—it’s a topic we both enjoyed because let’s be real, we were and still are madly in love with one another.
When I was visiting family in Chicago, I remember that all I wanted to do was put a ring on it/her (thank you, Beyoncé). When I came back to Portland, I took Jess on a little adventure to Shane Co., which led to us finding the perfect ring. What she didn’t know at the time was that I put the ring on layaway on my way to the bathroom while she continued looking. The ring had a classic white gold band and a princess cut diamond with a traditional architectural design.
It is simple, but it has intricacies. I felt the ring really emphasizes who she is as a person. We couldn’t have chosen a better one.
About Jess’ Ring:
This delicate vintage-inspired solitaire ring features a gorgeous princess cut diamond in a 14 karat white gold setting.
Take Shane Co.’s quiz to find out what engagement ring style is perfect for you.
Photos by Jenn Pacurar