The One With the Proposal
We made the ring together - I knew when he ordered it because I picked the diamond, I knew {about} when it should be ready because the store posts their delivery times for planning purposes, and so I painted my nails and I waited, I was ready - and twice I thought it was coming but then it didn’t happen. I told my friends, “I can’t believe this guy is making me wait!”
Fast forward to a Sunday where we had plans with our friends Connor and Lydia, which turned into plans with our friends Connor, Lydia, and Caleb, which turned into our friends coming over to hang out at our barely unpacked apartment. Evan kept giving vague details saying Lydia had planned something and she wanted it to be a surprise, and I do love surprises but man they also stress me out because I like to be comfortable and well prepared for things! He said he would tell me what we were doing if it would make me feel better but he thought it would be more fun if it was a surprise so I told him it was fine and carried on gathering things - Lydia had told us to collect a few personal items in a container.
Our friends showed up, we gave them a quick tour, and then the games began.. we were all asked to turn around while Lydia prepared the surprise.
When it was time to turn around, lo and behold, a TASKMASTER TASK was on the kitchen peninsula in front of me. I nearly wet myself with glee - “we’re playing Taskmaster?! Who gets to read the task?!”
I opened my very first Taskmaster task and read aloud, “Obscure an item set in Jello. Most difficult item for Connor to decipher wins. Bonus points if Connor must eat any Jello to determine the obscured item. You have 15 minutes to prepare the Jello and set an item. Your time starts now.” Lydia produced Jello from her bags of tricks, sent Connor away (literally out the door) and we went to work. When our time was up, we put the Jello in the freezer to help it set and then we turned around while Lydia prepared the next task.
Connor never returned, and I honestly was so immersed in the game I forgot he left. “Get the entire TP roll through the TP roll core. If you tear the roll, you must put your hands on your head and sing the alphabet song for 5 seconds before continuing. Fastest wins. Your time starts on the whistle.” Evan took a traditional approach of just speed and paying the consequences for rips, Caleb tried an abstract approach using water, and I was bound and determined to not rip the TP, which meant I came last.
We turned around again and watched Bentley make a bed in my intact but completely unrolled TP roll while Lydia prepared the next task. “Decorate this cake for Connor’s birthday. You have 3 minutes. Your time starts now.” Lydia had made three incredible looking (and smelling) Funfetti cakes as well as provided frosting, a plethora of sprinkles, utensils, and even gloves. The three of us immediately dove into the frosting and made some well decorated cakes. At the three minute mark - SURPRISE - a second envelope (the BEST kind of task). “Connor doesn’t want a birthday cake. Undecorate his cake and decorations to their original form. Best undecorated cake wins. You have 3 minutes. Your time starts now. Oh boy - I did not get very far in those three minutes because my brain broke. Evan and Caleb did pretty well but Evan really cleaned his cake off as though it had never been frosted. The guy was now 2 for 2!
We took a small break where I ate some cake, Lydia assembled her things, and we were told our next task was an outdoor task. “Are crocs appropriate?” I called from my closet. Lydia affirmed and we went on our way. I started to think something was up as we were walking but quickly pushed it down because there was no way this would all be for me or have anything to do with a proposal. I didn’t know how Lydia knew where she was taking us because she doesn’t live in our neighborhood, but she does like to walk and she seemed committed to the role so I just followed. Our next task arrived, “Take the most incognito photo with the cutest, stranger dog. Cutest and most incognito photo wins. You have 20 minutes to text the photo to Lydia and meet at the Blue Caboose. Your time starts now.” I immediately start explaining to Caleb and Evan where the Blue Caboose is since I thought they wouldn’t know, but it is on Google maps so they shrugged me off and we all ran our separate ways. I was certain I had the advantage here because I know where all the dogs are, but I also know all the dogs.. so it took my a bit to find a “stranger” dog and then it took me even longer to try to take my best incognito photo. I’d set a timer on my phone and those twenty minutes flew by in no time.
I arrived at the Blue Caboose and Lydia and Evan were already there, “This is a team task!” she announced, which explained why Caleb was now gone. Just like Connor’s disappearance, it didn’t phase me - I was focused and ready for the next task. “Open the Proper Box. Every time you open a yellow box you must name the box and gently pet it. Every time you open a red box you must clap for 10 seconds. Every time you open a black box you must give your teammate a dramatic, slow motion high five. Every time you open blue box you must earnestly compliment your teammate. Every time you open a pink box you must spin around 5 times. Every time you open a green box you must name three types of bread. Every time you open a purple box you must strike a pose. Your time starts now.” We could see a few boxes on the bench in front of us and others hidden around the area so we briefly discussed what the proper box could be and how we’d know, they all looked the same except they were different colors. We opened the first one and there was a letter on the lid and a piece of paper in the inside that had a random phrase on the front (like “That’s a bold opinion for someone wearing Crocs in public!”) and parts of letters on the back - so clearly we were supposed to put a puzzle together to find the proper box. After we figured that out, we went to town opening boxes and doing all of the tasks that came along with that - so many slow motion high fives! It was a very blustery day so we were struggling but Lydia had tape and Evan thought we should focus on the box tops instead of the papers so we started trying to get a phrase and he walked me into getting “art installation.” There’s an art installation that’s part of the harbor walk area near our apartment complex so we ran to it and could see Connor holding a box and turning around in circles - hey, Connor is here! We opened the box that Connor was holding, which gave way to another box, and then another box, and then another box.. each taunting us at not being the Proper Box and each bearing a color that required us to perform an action.
Finally, the smallest box had the smallest message in the smallest print - “The Proper Box is where mozzarella meets meat.” The bridge between Mida, the Italian restaurant, and the Smokehouse BBQ restaurant. The bridge where we had our first kiss. At this point I knew but I still wouldn’t let myself believe this was actually happening to me.. I squeezed Evan’s hand so tight as we walked down the harbor walk, and when we rounded the corner and I saw the bridge decorated with an assortment of flowers I lost it. There on the bridge where we shared our first kiss were four vases full of beautiful roses and a large box in the middle. I opened it, and it was red so I clapped for 10 seconds. The message inside read, “This is a very Proper Box, now turn around.” There in front of me on one knee was the love of my life, my favorite person and best friend, Evan.
Of course I said yes, and it took me a minute to process everything, but you know I took a moment to admire my girl, the RING! I was so excited to see her in real life - she’s gorgeous. We kissed on our bridge and Evan pointed out Caleb up the stairs who had recorded the whole thing. Lydia took pictures of us on our bridge, we walked back to our apartment and shared our joy together with our friends and talked about how amazing and fun the day was and how Evan had planned everything months prior with help from our friends and then had tried to execute it a couple other times but it had fallen through. My nails weren’t done but I didn’t care, it was the best day of my life. I still can’t believe that he (and Lydia, Caleb, and Connor) did all of that just for me. I am the luckiest girl in the world.
Later on we went downstairs to buy a bottle of champagne and lo and behold my BFF Brigid (& her boyfriend Ash) pulled up on the corner with flowers and hugs! What a wonderful surprise and fun way to continue the celebration.
The next day we got to call everyone and share the news - best phone calls ever! I will never forget this time in my life and I’m so thankful to have the photos and videos to remember. <3
Evan proposed to Melissa June 1st, 2025 in Boston, MA.