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We can't wait to celebrate with you!
We can't wait to celebrate with you!

Tyler & Keira

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Tyler

Highbaugh

and

Keira

Gilmore

December 31, 2024

Chicago, IL

How We Met

Who says you can't find love in college?

Tyler and I met in the spring of 2015 while I was attending a party with my sorority sisters. We made a brief connection that night, but never actually held a conversation. In the fall once we had returned to campus for the next semester, Tyler had ironically moved next door to me. One day, I was sitting in my car chatting with a friend, when he knocked on my window to ask for my number. He claimed he wanted to invite me to a welcome week party he was cohosting with his roommates. I never intended on attending the party but gave him my number anyway. After years of a flirtatious friendship, and a finance and healthcare class that brought us closer together, we decided we didn't want to be friends anymore. NYE 2018, we made it official ❤️✨

The Proposal

Love in Paradise

Keira and I had planned a trip to Montego Bay to celebrate her birthday, and for me successfully completing my MBA program in May… but I also had something else planned up my sleeve. For months a particular Tiffany yellow diamond ring Keira expressed her interest in years ago sat and burned a hole in my pocket, but I wanted to make sure the moment was special. And what’s more special than a beach proposal in Jamaica?! A few days before arriving, I scheduled a surprise lavish beach dinner through our friendly staff at our resort which was going to be a perfect set up to pop the question. Everything was aligned and planned out, until about 12 hours before the reservation. I had received a note from the resort staff that they had to cancel the beach dinner due to a lack of personal staff available. Talk about stressed! Luckily, I was led in the right direction to someone who helped me come up with a plan B, which arguably may be better than the first idea. Imagine one evening walking along a rose petal walkway on the beach leading to a giant LED lit gazebo with a sign asking “Will you marry me”, along with a 4-foot-tall lit ring prop💍… oh and two flutes of champagne of course😉. Keira said yes 6/10/2023, and I’ve been counting down the days I can call her my wife 👰🏽‍♀️ ever since!

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For all the days along the way
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