Jill and Jason

How We Met

Jason and I met “officially” at a party the summer after I graduated high school. We grew up in a small town and he was my friend’s older brother, and my older brother’s friend, so we knew who each other was, but we didn’t actually speak until the night of that party. Nextel was “the thing” back then so we both had Nextel phones and he tricked me into putting his Direct Connect number in my phone and pushing the button. He was really sweet that whole night, and as I learned, he was the life of the party, as always. The next day I was at work and he started to “beep” me! Knowing his reputation, I immediately thought I did something wrong and he was mad at me, so I stepped out of the office and answered his beep, but apparently all he wanted to do was say hi. For the rest of that summer we kept beeping each other and texting and finally went on our first date to Four Brothers Pizzaria. Toward the end of the summer we went to the Dutchess County Fair and that was the first place we held hands so it will always hold a special space in my heart!

Summer came to an end and I went away to my freshman year of college, 4 hours away, and he stayed home to work. We spoke as much as we could through that first semester and tried to visit but ended up realizing how difficult it would be to have a long distance relationship and decided it wasn’t a good idea by the time the semester ended. From that point forward we both TRIED to not to talk to each other for years but kind of failed at that. When my junior year rolled around we reconnected in person and decided we couldn’t deny it any longer, but the long distance didn’t end there…in fact it got further as I went to study abroad in AUSTRALIA. We spoke first thing in the morning or late at night, depending on which time zone you’re referencing, each day and he even picked me up from the airport when I finally come home for the summer. After that I had enough credits to only need one more semester my senior year and he helped move me out of college and we’ve been inseparable ever since.

Fast forward, we’ve been together for five and a half years, just bought a house together and have our two furbaby dogs, so what more would we need other than a ring?

How He Asked

Jason and I had always sort of talked about things that I wish would happen if he ever decided to propose. I told him what I wished my ring would look like, that I wished I would look nice and someone would be there to take a picture, I told him it would be cool if my best friend could be there and even cooler if it were a place with a view since we both love hiking, but it’s not like I’d say no if none of this happened! All along he’d always quickly end the conversation, brushing it off and making me feel like we were not getting engaged for a VERY long time.

I had been planning to have my best friend from college come visit me for quite some time, and we landed on a long weekend in the middle of July so she could come see our new house and our surprise puppy (a last minute decision I’d been begging for since we bought our home)! I began looking around for Groupons and found one for a Distillery right down the road from our house and a Winery in Millbrook so we decided to go on a tasting tour as something to do while she was in town. Jason had wanted his friend Brian to come so he wouldn’t feel like the third wheel with me and Natasha (it totally happens)!

A few days before THE day, Jason’s had stopped eating the lunches I was making him and I was getting mad I was throwing out perfectly good food at the end of the day that had spoiled in the heat. Turns out he was just nervous and couldn’t eat!

The day had come and my original plans to start at Millbrook and end closer to our house were flopped upside down when Jason decided to do it in the opposite order for reasons I couldn’t figure out. We spent the day tasting different bourbons and wines and just enjoying the afternoon.

Where to Propose in Millbrook Vinyards and Winery

Engagement Proposal Ideas in Millbrook Vinyards and Winery

Wedding Proposal Ideas in Millbrook Vinyards and Winery

When we got to Millbrook Winery and Vineyards we decided to forget about the tasting and just get lunch outside. While eating lunch Natasha pointed out the trail we could take to a viewpoint, so we decided to do it after we finished eating. Of course, Jason didn’t finish eating and claimed he was feeling nauseous so I just assumed it was from the alcohol! Natasha and I finished our wine while the boys went inside to buy bottles to take home. When they came back with their bag in hand, we started to walk toward the trail, Natasha, and I in front, and Brian and Jason and back. I decided to cut through an opening in the pathway while everyone else went the long way around, and when they all caught up we started to take pictures like we had been doing all day, nothing out of the ordinary. Natasha and I took some pictures together, and then it was Jason in my turn, and then it happened.

Marriage Proposal Ideas in Millbrook Vinyards and Winery

Brian and Natasha were taking pictures of us (and were in on it the whole time) and directed us to take one with the bottle so, me being me, I grabbed the wrong bottle and they said “no the Chardonnay!” So I took out the right bottle and walked to stand next to Jason again and everybody asked me what the bottle said, and as I read the sticker on the bottle I looked down and Jason’s on one knee with the most gorgeous ring I’ve ever seen in his hand. I couldn’t believe it for one second and asked him if it was really happening, it took me a while of hugging and kissing and crying until I finally said “well yeah!” I’d like to say everyone was crying but to be honest, all I could see was Jason and both of us were crying.

It was the biggest surprise, and the perfect engagement with a beautiful view, a cute new dress, the perfect ring, a lot of great pictures, and my best friend. Brian and Natasha left us in the vineyard for a little while and then it started to rain which I thought was the best sign possible because I absolutely love rain. When we came down we cheers’ed over another bottle of wine and Jason told me how he asked my parents permission on Thursday and that’s why he hasn’t been eating lunch, and that my parents were going to be waiting at our house for us when we get home. I never thought I wanted him to ask for permission, I always thought I wanted to be the first one to know I was getting engaged, but I’m so glad he didn’t listen to me! We had a wonderful night celebrating with my parents and are two good friends and I couldn’t have asked for anything more perfect. I can’t wait to marry the man of my dreams.