Rachael and Matt

How We Met

We were hired the same year at an independent boarding school near beautiful Mount Monadnock, and we worked there for a year as colleagues. The summer before our second year working there, things changed. When we had our August faculty PD days, in the mandatory meeting, Matt jumped over a row of auditorium seats to sit next to me. In a soccer warm-up bonding exercise, Matt moved to be my partner. Both of us had a new easiness of conversation, a new giddy nervousness, a new spark.

Then, when we had a faculty Work Gang session, the Head of School was splitting us into teams. One team was moving camping supplies from the Maintenance Shed. Another group was clearing trails. Another was setting up and organizing tents. Another was painting the fences on Upper Field.

Matt was sitting across from me in the faculty circle, and he saw my face light up; I definitely wanted to be placed in the fence painting group. I raised my hand, and Matt snuck across the circle to sit next to me and raised his hand to join the fence painting group as well. It was a warm, blue-sky day, and we worked alongside each other painting the wooden fence white. We laughed and talked and smiled and painted.

Then Matt asked me out to dinner, and I promptly freaked out. My friend came over to do my hair; she used a curling wand and put mascara on me extra carefully. I put on a red dress and hoped that Matt would also be a little dressed up. My friend and I laughed that Matt always wore his “Matt outfit”—a black crew-neck t-shirt and jeans. She said, “If he is wearing something other than that, he really likes you.”

Matt arrived to my door. He was wearing a green and blue checkered button-up shirt. He looked so nice. And nervous. No “Matt outfit.”

We went to dinner, and we talked for four hours. We sat by the window. We discussed everything.

We were quickly realizing we had found our person, sitting right across the table. That night, we decided that we would go on our second date the next day—a hike! Since our school was so close to Mount Monadnock, we would go there.

Proposal Ideas Mount Monadnock

That hike was where we fell in love, and the rest is history.

How He Asked

Fast forward about two years. Matt and I live together in a little red house with our cat Virginia Woolf and our puppy Macy. On weekends, especially in the summer, we like to sleep in, then wake up, listen to jazz or Beyoncé or a fun, dancey playlist, go for a workout, and then make or go out for a late breakfast.

On this particular Sunday, Matt woke me up at 6am to go on a hike. It was one of the warmest days in July, so he wanted to start on our adventure early. He asked me to get dressed in outdoor clothes and hiking shoes. When we started driving, I could tell we were headed to Mount Monadnock—the Dublin Trail.

The trail was nearly empty, and everything was lush and green.

As we began to walk, Matt said that sometimes the mountain helps us when we have a really important message to share, and if we look carefully, we might find messages along the way.

With some directing—and a few laughs, Matt helped me see the yellow ribbon tied around a tree. He guided me to search around this tree, and in a few minutes, I discovered a Ziplock-bag covered envelope that was buried under loose stones. I opened the envelope, my heart racing, and started to read.

There were six envelopes lining the trail on the hike up, each marked with yellow-clad trees. Each envelope had a single word—a theme—written on it, and, inside each, I found a two-page love letter.

The letters were thoughtful and heartfelt and precise, full of so much love and all different emotion. Some parts made me laugh, others made me cry. They referenced our early days of dating, some of the most magical times in our lives, and some of the most difficult times. They told stories of what matters to us, and they showed me, so genuinely and perfectly, how much I mean to Matt. The story of these letters told in the theme written across each envelope, moved from Kindness to Beauty, to Intelligence, to Importance, to Family, and, last, to Partnership.

At the top of Monadnock, after an amazing journey through the letters and through the simultaneous memory of our second date hike, Matt took me to a ledge where we had once sat to do deep breathing exercises. He asked me to stand and take a few deep breaths, and when I looked down, he was on one knee.

When I said yes, a crowd of strangers around the peak of the mountain started cheering from above.

Our hearts are so full. I am so, so thrilled that we found each other and that we have these beautiful letters to tell the story of our love.

Special Thanks

Henry + Mac
Photographer