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Jill & Sam

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Jill Montellano

&

Sam Gleason

#jillandsamswedding

August 17, 2025

San Francisco, CA

The Proposal

November 6, 2024

Sam is terrible at keeping secrets. That’s why I, Jill, knew that he was going to propose to me for about a month before he actually did so. One October morning Sam told me he was going to swim practice… but almost immediately after that he told me that actually he’s going to pick up the engagement ring that he had ordered. He also told me to still act surprised when he pops the question. For weeks I wondered if today was going to be THE day. Sam cleverly enlisted the help of Jessica (my sister/MOH) to catch me off guard with his proposal. Jessica invited me to go with her to take pictures around the Palace of Fine Arts in San Francisco, and little did I know that Sam would be joining us just a bit later. It took me a few full seconds to realize that it was really Sam and not just a lookalike coming around the corner of the rotunda, and it took me even longer to comprehend what he was saying once he got down on one knee. Thankfully he had many sweet things to say, so my mind had time to catch up with us in time for him to ask me to marry him, and for me to immediately say, “Yes!”

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