The Proposal
I proposed at the Yankees/Astros game — we've seen countless games together and it's one of our favorite date spots (George is a lifetime Yankees fan and Kate was a quick convert, especially when she learned Aaron Judge has two mini Dachshunds; we only have the one).
I enlisted the help of my head of HR to send me a fake email claiming I won the 2 tickets from a company raffle (to throw her off the scent even more) I insisted we get Cracker Jacks and broke them out in the bottom of the 1st inning. I said "I think there's a prize inside!" Pretending to pull the ring from the bag. After Kate said yes, all of her friends and mine (16 of them in all!) rushed down the stairs to surprise her for the second time in as many minutes. Even her sister (who flew out from Wisconsin) was there to join. After the game, we had an "impromptu" engagement party with friends back at our apartment. Little did Kate know her two best friends from Indiana were waiting for us there, ready with bottles of champagne.