Matthew and Chelsey

Engagement Proposal Ideas in Massachussetts

How we met

Growing up together in the same hometown, attending the same schools and sporting events, and having mutual friends makes it almost impossible to think of a time that we didn’t at least know of each other. But, our love story began about seven years ago in high school. Spring was in the air and everyone was just itching for the day’s final bell to ring. Getting a head start, I strolled down what I thought was an empty hall. I turned the corner to my locker and there was Matt… he was fuddling with an orange doodle-covered binder standing tall and goofy but so handsome with his bleach blonde hair and incredibly welcoming smile – I swore I had never seen a more perfect human being. It was then I knew there was something special about this person and I need to know more about him.

Chelsea and Groom's Engagement in Massachussetts

We were inseparable after our first meeting: family events, proms, countless dates and growing up together through the rest of our teenage years. After graduating, our journey together continued as we attended the same college. The more I got to know him, I could tell he was the most loving and understanding guy I could ever ask for. I knew I loved Matt pretty much right away. It was at his eldest brother’s wedding; we were slow-dancing together when I thought to myself, “Wow, I love this guy and I’ll be so lucky if this is us someday.”

Proposal Ideas Massachussetts

How he asked

An October’s weekend getaway to Vermont for all things fall and foliage is what brought us to Woodstock’s most charming inn; or so that is what I had thought. After an incredibly fun day, Matt and I returned to the inn to get ready for our dinner reservation. I walked up the winding stairs to find our door shut with its antique key in the lock and a card leaning against the door. As I bent down in the hallway to pick up the card I was thinking to myself, I am so incredibly lucky to be here with the most amazing guy. I began to read the sweet card full of loving thoughts, when it began to sink in… “What? Wait, oh my gosh! It’s really happening!” (I never even saw it coming!)

Tears began to well up in my eyes when I saw on the inside of this card was a 5-year-old grease-splattered green sticky note with my handwriting on it. It was the note I had put inside of a snack-bag of goldfish asking him to my senior prom saying: “Of all the fish in the sea will you go to prom with me? Check yes / no”

I lost my breath. Not only because he had thought to save this note, but because underneath this sticky note was a new one from Matt: “Of all the fish in the sea, will you be my wife and marry me?” I opened the most magical door to find a romantic fire burning, Brett Eldredge’s ‘Wanna be That Song’ playing in the background and my sweet Matt with his amazing smile bending down onto one knee.

We’re so excited to start our lives together. We are currently planning a paradise wedding in Key West in 2018, so we wanted our engagement shoot to nod to winter in New England!

Special Thanks