A woman was on the verge of crying joyous tears every step of the way when her middle school sweetheart planned a scavenger hunt across town and some of their most memorable spots, leading to a surprise proposal.
Kristen DeCicco, 25, met her now-fiancé, James Silberger, 26, in a 7th-grade math class. They soon became boyfriend and girlfriend.
Having been with Kristen for over half his life, James created a proposal incorporating the key spots where so many of their most precious memories had taken place.
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On September 8, the pair’s first stop was Woodmere Middle School in Hewlett, New York, where they met and where Kristen thought she was headed to play sports with her family.
When Kristen and her siblings are all home, it’s not uncommon for them all to play tennis, football, or pickleball together, so she didn’t expect anything when James took her to school to do so.
But when an unsuspecting Kristen, dressed in workout clothes, arrived, she was greeted by a selection of photos and roses, set up by her sister, Samantha.
Kristen couldn’t believe her eyes, joking that she was being proposed to in workout gear—but James revealed that was only part of the surprise.
The scavenger hunt then took Kristen to her parents’ home, where the couple shared their first kiss; saw her get styled by her friends, who helped her pick out a dress for the big occasion; and onto Woodmere Docks, to symbolize the first vacation the couple took together on a cruise.
Each step of the way, Kristen was being handed a clue by family members, and it was then on to the local lacrosse field, where James had asked her to prom, before she was taken to the spot of a local ice rink, which, James said, symbolized the couple’s love of the New York Islanders.
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Then, for the final clue, Kristen was told that she would be going on a boat ride. This was a hobby she, James, and James’ dad would often do, and she thought it was a fitting end.
But when she reached the waterfront, Kristen was instead met with a red carpet, leading to James and a series of large letters that read “Marry Me.”
James then got down on one knee as a tearful Kirsten said yes as he asked her the big question.
Samantha and Kirsten captured the emotional scavenger hunt and its romantic ending on video and later shared a video of the stages on social media.
Kirsten and James are planning for their wedding to be around their anniversary, November 1, 2025.
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She said: “There was a lot of thought and planning that went into the extravagant scavenger hunt proposal.
“James had help from both my mother and sister to make the day run smoothly, and he came up with each clue to symbolize a special moment and place in our relationship.
“Posting the video on social media was something we chose to do to announce that we were engaged.
“I was so excited to share the video because it was truly the best day ever.
“We have gotten so many responses about the proposal and so much love from friends and family.
“We even had tons of strangers reach out to congratulate us and tell us that it was the best proposal they had seen. “It was truly special to see so many people watch our video.”
