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September 18, 2021
Lloyd Harbor, New York

Kelsey & Jason

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Jason Santana

and

Kelsey De Rosa

September 18, 2021

Lloyd Harbor, New York

The Proposal

November 25th, 2020

In preparation for the proposal, a ton of lying went on in order for it all to happen – I am very thankful to Kelsey for forgiving me! There were a few things that were absolute when it came to asking Kelsey to marry me: asking her parents for their blessing, having her family with us whenever I proposed, meeting all of her closest friends and family, and to SURPRISE HER. I set out to accomplish all of that, leading me to the week of Thanksgiving. Having secured the ring (with help from Corinne and the Neels), I asked my parents if they would be willing to head to New York for the engagement; they would be able to meet David and Denise, surprise Kelsey even more with them being there, and spend the holiday with the De Rosa’s. They were onboard. Next up was how I would be able to ask for her parent’s blessing. I told Kelsey I was going camping with a buddy of mine; I would leave early in the morning on Saturday and get back in the afternoon on Sunday. Little did she know, I booked a flight to New York to ask her parents for their blessing, & was back in time for church on Sunday. I then had many conversations with Kelsey’s brother, sister, best friends. . . All of whom I could not have done any of this without. & with that the proposal was set. On Monday, November 23rd, my dad and I drove from Chicago to Long Island and my mom flew in the day after. We all stayed in hiding at one of David’s properties, which gave me time to get everything ready for the proposal. The waiting was the worst part. And the rest is history – David drove Kelsey and the whole gang to Fort Hill and was met by my car parked right out in front with the first of my “breadcrumbs” that led Kelsey on a path straight to me. Sometimes a flower and note led Kelsey on her way, other times it was a surprise guest. But regardless, it led to a question at the end. And I think you know what she said.

For all the days along the way
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