Deanna and Tyler

Engagement Proposal Ideas in Martha's Vineyard, Massachusetts

How We Met

Tyler and I met in March of 2014, we sat just a few feet away from each other at work. Believe it or not, we sat next to each other for 6 months and had never met, but one day our paths finally crossed, our eyes met and I thought to myself “wow, that guy that sits next to me is really cute!”. The flirting began right there – who began flirting with who first, that depends on who you ask. ;) It began with instant messages and running out for coffee breaks and a few days later he asked me to join him and his friends for a night out in Boston. I grabbed one of my girlfriends and joined him at Landsdowne Pub near Fenway Park in Boston for a night full a dancing right in front of the fantastic live band and singing our hears out. His energy was magnetic, after hours of dancing and laughing we shared our first kiss. On the ride home that night I had a smile pinned to my face, I knew I had met someone very special.

Where to Propose in Martha's Vineyard, Massachusetts

The next few weeks were full of more of those quick coffee dates at work and phone calls until Tyler asked me on our first real date – Five Horses in Davis Square, Somerville Ma. Our date was quickly followed by a ski trip the next weekend to Sunday River in Maine where I met a long list of Sleeper family members and was introduced (to my ecstatic surprise) as his girlfriend. The weeks began to fly by and before I knew it, it was early May, we were sitting on the front of a boat, in Tashmoo on Martha’s Vineyard and this incredibly handsome new boyfriend of mine said “I love you” for the very first time.

Marriage Proposal Ideas in Martha's Vineyard, Massachusetts

The years have been nothing but love and excitement from there. We have continued to grow into each other’s best friend and spend our weekends filling them with as many family and friends as we can find. Tyler has coached me into a pretty darn good skier if I do say so myself in the winters, and in the summers you can find us chasing as much sunshine as possible all over Cape Cod. Tyler is the most lovable, thoughtful and compassionate person I have ever met, he is my biggest supporter and strongest advocate, he brings light to every room and the fun to every party, he finds the positive in any situation and the love of my life. I am lucky to get to call his arms, my home – forever.

Proposal Ideas Martha's Vineyard, Massachusetts

Deanna's Proposal in Martha's Vineyard, Massachusetts

As my mom has said from the very beginning – “Sleeper is a keeper!”

How He Asked

Tyler planned a surprise weekend on Martha’s Vineyard to celebrate my 25th birthday. We stayed at hotel Summer Camp in Oak Bluffs and rented a Jeep Wrangler for the day to explore all of our favorite spots on the island. The weather had been dark and rainy for days but on that Sunday morning, we woke up to bright sunshine. We kicked off the morning with my favorite breakfast at The Black Dog and then hopped in the Jeep to start our day. First stop, our favorite spot – Tashmoo.

We parked right there on the sand and Tyler suggested we prop his GoPro up on the hood to snap a picture. We stepped out towards the shoreline and both took a moment to appreciate the outstanding view of the bay from that spot. Tyler then turns to me over his right shoulder and says “D, you’ve been my best friend for the last 3 years”. Before I knew it he was down on one knee, my eyes were filled with tears and I was shaking while trying my hardest to focus on his growing smile and impressively calm speech.

“Deanna, will you spend forever with me?”

By this point, my emotions were bubbling over and I was a combination of laughing and crying at once but I finally put both hands on his cheeks and said YES!

We spent the next few minutes hugging before I said “Let me see it!” remembering that he was still holding an engagement ring in his left hand while wrapping me in the tightest hug.

Tashmoo on Martha’s Vineyard has always been a special place for us, it is home to an important chapter of our love story, our very first “I Love You” and now our engagement.

We spent the rest of the day enjoying our time on the island, stopping in at the fishing village of Menemsha for lunch (lobster roll and oysters, our favorite!) and soaking up the sheer bliss of our day.

The following 48 hours have been filled with an outpouring of love and support in celebration of our engagement by both of our families and our friends, we are so very lucky.