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Annie Lyn & Jake

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Jake Otten

&

Annie Lyn Sheketoff

October 18, 2025

Lake George, NY
143 days143 d1 hour1 h26 minutes26 min42 seconds42 s

The Proposal

High School Sweethearts

My goal was to keep her in the dark throughout the entire process. Between hiding messages with the jeweler and the photographer, to disguising my incognito NYC diamond district trips as client house calls, there were too many close calls that I thought enough was enough. I hadn’t even had the ring for 12 hours when I called her on May 29th, in the middle of the day and asked if dinner tonight could be fit into her busy schedule. The upcoming weekend brought multiple events with friends and family that I knew the time had to be now. Luckily, she agreed to dinner at a new spot downtown. Date and time had been set, now it was a matter of execution. For the days leading up, I had my eye on a nearby park that looked beautiful when the evening sun peeked through the trees and glimmered on the pond. It was the end of May, so the weather was warm and the flowers were in full bloom. I had the exact spot I wanted picked out and communicated to the photographer that today was the day as Annie Lyn was getting ready in the other room. What a saint that guy was. The park was near the restaurant, so I played it off that the street parking was brutal, and that we should park behind the park and walk to dinner. Annie Lyn, being the sweetheart she is, met me with no resistance to this proposition. Thank God. As we got out of the car, I slipped the ring in my back left pocket. Although, I wish I had a pocket for my heart because it was beating out of my chest. Annie Lyn started talking to me about how pretty the park was, and was asking questions about some of the plant life on the bank of the pond. I, deafened by my racing mind reciting the lines I wished to remember, must have answered her with complete gibberish. We continued down the trail to where I wanted us to be, I got down on one knee, and the photographer popped out from behind a tree as I tried my best to articulate how much she meant to me. The moment was beautiful and unforgettable, and the lead up of stress paled in comparison to the feelings we both felt! We left the park on cloud 9 and made it over to dinner, FaceTiming family and sharing the news. It was perfect! We both took the following day off to celebrate the beginning of forever!

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For all the days along the way
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