When Emma told me about her dream proposal, it had two simple components: She always dreamed that it would be a surprise and that we would look nice. No problem, right? Well, cue a global pandemic that locked us in our homes for months. Suddenly, deciding to get out of pajamas counted as dressing up, and walking the dog on a new route was an exciting twist. It doesn’t help that Emma is already basically Sherlock Holmes when it comes to surprises, and I'm not exactly the sneakiest, quietest guy in the world... Just like in a movie, I was going to need a team. Luckily, I had a ready and willing family to help out, though I’m not sure they knew what they signed up for. This moment was really important to Emma and me, and I really wanted to get it right. Everyone brought their own ideas to get the final plan: Theresa and dad would pretend to throw an art show in their town by the lake. My mom would watch our dog Pablo and suggest a dinner place for the night so we would finally put away the pjs. Ailene would get the food for the surprise party and sneak some photos. Pablo would look cute and be a dog. It was all coming together...

So many things nearly went wrong including some accidental texts, a push notification when Emma gained a new follower to her wedding ring Pinterest board, and some close calls with my poor ring-hiding decisions. But the day got closer and it seemed that Emma hadn’t caught on, or at least thought she had a few months to go. The day of the engagement, everything went according to plan! After dropping Pablo off for our dinner out, we headed down to the “art show” by the lake for a quick stop. I nervously got down on one knee by the beautiful lake and did my speech. Emma was so excited she could not stop interrupting and asking if this was real (we did a second version of the proposal later so she could actually hear what I said!), but she did get her line right… “YES!” Ailene and Theresa “stealthily” took some beautiful photos, and then we headed to our dinner date- which was actually a surprise party, not a date at all! Back at Casa Orr we met up with my parents and Emma’s sister and her boyfriend in my parents’ yard which we had spent all day decorating. We had champagne and then video chatted with Emma’s entire family. I had asked if her mom and grandparents might want to be a part of the moment, but the surprises kept coming as everyone jumped online to say congratulations! It was a memorable, special night that we will never forget, made even more important because so many people helped make it a success. Of course, afterwards Emma told me she was suspicious the entire time and that I was acting like a nervous weirdo all day. But it was sweet of her to let me feel like I succeeded for a bit. At least we both looked nice!