How Matt Popped The Question, And I Said, “Yes!”

Proposal stories are some of my favorites to read! The other day I realized I never shared the story of exactly how Matt proposed to me back in October 2020. Since Fall is such an exciting and hectic time for […]

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Proposal stories are some of my favorites to read! The other day I realized I never shared the story of exactly how Matt proposed to me back in October 2020. Since Fall is such an exciting and hectic time for both Matt and me, I didn’t get a chance to sit down and share the details – until now! I’m a big believer in better late than never. That’s why today I’m sharing with you how Matt popped the question and I (of course) said, “yes!”


The weekend of Matt’s proposal he decided to take me on a somewhat spontaneous trip up north. I say somewhat because Matt is really bad at keeping secrets, like so bad. I have to admit he did a really good job at keeping our destination a secret. That is, until the day before our trip when he casually said the weather looks great in New Hampshire for our weekend.


So, needless to say, I knew we were headed to New Hampshire. Other than the destination I had no idea what the itinerary was which was really exciting – since I’m such a planner and usually am the ones making all the plans!

We couldn’t have had a more beautiful weekend.

With stunning foliage and crisp fall air, I couldn’t help but bring my camera along to leaf peep. We started our trip up north by stopping at Boulevard Diner in Worcester, MA – a place I’d never been. Not only is it a pretty renowned diner, founded in 1930, but it’s actually located in a vintage train car. Plus, it’s open 24/7 and constantly dishing out the best diner food. When Matt told me we were making a pit stop for food, I thought maybe a quick stop at Dunkin – so I was very surprised and giddy to find out we were stopping for a sit-down breakfast experience – at a diner which is my favorite place to eat!

After omelets and diner coffee we drove a couple more hours north until we were in New Hampshire. And onto our next stop at @macksapplesnh in Londonderry.  As one of New Hampshire’s oldest family-fun farms, @macksapplesnh has been on my bucket list to visit for quite some time. Between the diner and the apple orchard, the weekend could have ended there any been magical. The best part is Matt gave me plenty of time to pick apples, pumpkins, and pears along with a quick photoshoot for the blog which you can see in our 5 apple orchards to visit in New England this fall post.

Matt was pulling out all the stops and smiling all along the way!

Matt graciously drove me down some back roads to leaf peep our way to our next destination: Matt’s parent’s condo on Lake Winnipesaukee. Truthfully, I was a little confused as to where we were headed next because Matt kept bringing up how excited he was along with telling me never to look in the trunk and that dinner was going to be fancy, but sweatpants were optional.

As it started to get dark, we headed out and picked up Italian food to go. Then after a sunset ride around Weirs Beach – we ended up at the Weirs Drive-Inn for a spooky double-feature. Plus, I got to personally pick the double-feature! Of course, I chose Hocus Pocus and Little Shops Of Horror. Matt didn’t complain once! Not when he realized Little Shops Of Horrors was a musical; not when we accidentally drained his battery and we had to jump his car; no negative Mr. Matt!

Now, will I get him to watch Little Shops Of Horror with me again? Probably not. But, at least it happened once! I’m a huge fan of all the spooky cult movies so I’m glad Matt got to watch with me. Can you believe he had never seen Hocus Pocus?!

The next day, Matt was hemming and hawing over whether we should grab breakfast at a place I had written about or grab breakfast on-route to our next stop. I opted to get breakfast at the place I had written about because I was curious where we were headed.

I have written about so many restaurants, that I really had no idea we were headed to Heritage Pancake Farm. All I can say though is I’m obsessed because you can’t find a more authentic New England farm experience than Heritage Farm Pancake House.

Living up to their name, the farmhouses on-site live animals. Visitors can sneak a peek inside the sugar house where maple syrup is processed, and as for the food – everything is served family-style. The diverse menu includes 30 different flavors of pancakes and bacon to die for. The bacon was seriously so good

After breakfast, I wasn’t sure where we were headed, but we ended up taking a very long scenic foliage drive from New Hampshire through Vermont until we ended up in Deerfield Massachusetts. I was kind of surprised when we ended up at Deerfield, MA. I thought maybe he was taking me here for pictures but I should have known we were headed to the Mecca of leaf-peeping: The Yankee Candle Factory. The candle trip was worth it, as I haven’t been in there in forever.

Finally, it was getting late so we headed home and I have to admit, I was a little surprised that we were just going home – as I suspected he was going to propose.


After a weekend filled with fall festivities and a leaf-peeping road trip through Massachusetts, Vermont, and New Hampshire – Matt proposed on the small green in the town we grew up in. Which is also the town we currently reside.

It was just us, which was lucky for Matt because more often than not there are usually people walking, reading, and enjoying the fall foliage. I have no pictures of the actual engagement because my only request was to keep it between just Matt and me. No family. No photographers. We take photos all the time for the blog and I just didn’t want the engagement to feel like ‘work.’

Right after I said “yes,” Matt decided he had to tell our parents. I could have kept the secret till the next day but Matt got right on his phone and called over his grandparents, parents, and my parents to meet at our house – he was beyond excited to show them the ring and break the news.

It was a great night that ended with the most delicious roast dinner and chocolate dessert at one of our favorite restaurants, The Charles.

Overall it was a fun weekend that very much was “Matt and I.” Just us, enjoying the little things of fall and saying “yes” to continuing to write the next chapter of life together.


Earlier this year I shared how Matt proposed to me in October 2020. When I first shared the news, I received a lot of questions from you all about the ring! So, today I’m sharing a little background on my engagement ring, how Matt designed it, and why I went with more of a unique diamond cut. 

First things first! Matt was very stealthy in figuring out the engagement ring style I’d want. He commissioned my friend Jennifer, to scope out the details. Now let me tell you, I had no clue she was in cahoots with Matt. Still, I went about sending her a bunch of pictures I found of marquise diamond rings from Pinterest.

I always knew I wanted a marquise diamond, I just love the antique style and french historical roots. Plus, my Mom has a marquise diamond. Out of all the pictures, one specific picture stood out to me. It was a marquise diamond set in white gold with a gold band and bullet diamonds. I loved the retro feel of the bullet diamonds and the simplicity of a gold band.

I always envisioned an engagement ring that would be passed down as a family heirloom. A piece that was unique and fun!

Matt went on to compile his notes and the picture I had sent Jennifer and headed up to Boston to design the ring. His family actually has a tradition of going to Descenza in the city of Boston. Matt’s grandfather got his grandmother’s ring there. His parents got their ring there. And even Matt’s sister’s engagement ring is from there.

Traditions like this – for me – make the ring that much more special.

Matt called ahead to see if they had any marquise diamonds – as they’re less popular. Luckily, they had a few he could take a look at. After a few trips to Boston, the ring was complete. I’ll forever be astonished with the thought, effort, and deliberation Matt put into my ring.

I think he was really nervous it wouldn’t be what I wanted or what I had imagined. Marquise comes in a really large variety of shapes and he hit the nail on the head. 

To me, the ring is perfect. 

The funny part is Matt would tell me all the time that he was not a fan of the marquise. Still, he did design a marquise ring for me. And even if it’s not the ring he imagined – it’s so special to me!

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