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September 26, 2026
Sabillasville, MD

Our Greatest Adventure

Olivia Cleckner

and

Sean Updike

September 26, 2026

Sabillasville, MD
173 days173 d11 hours11 h45 minutes45 min19 seconds19 s

Our Story:

It's a story they love to tell because of its "kismet" nature. Back in the late 90's, Liv's mom ran an at-home daycare. The Updikes were one of her first clients, making Sean and Liv daycare buddies as infants. Despite not staying in touch as they grew up, they knew of each other thanks to the stories their parents shared, and hours of VHS tape footage Liv's mom still has. As teenagers, they ran into each other once at a Merriweather concert. Sean was popular, Liv was not - so, she got a picture with him and posted it on Instagram to prove boys actually talked to her. Throughout college, Liv often heard of Sean, and his humor, from friends with Howard County or University of Maryland connections. Although they likely attended some of the same UMD tailgates or nights out at RJ Bently's, it wasn't until after college that Liv and Sean got back in touch. Liv noticed that the boy she went to daycare with started liking an uncanny number of her tweets. A few Twitter DMs later, they finally exchanged numbers after technically knowing (of) each other for over 20 years. During Labor Day Weekend in 2020, they realized that they were both in Ocean City at the same time and planned to meet at Sandbar - a hole in the wall karaoke bar that they do not recommend visiting while sober. Liv was too nervous to approach Sean at first, and after pretending to play pool for 30 mins (it was the height of COVID - the bar removed the pool balls and sticks), her best friend, Kirsten, had enough of the coy games and walked over to Sean's table. Liv shyly followed. After some drinks, a few laughs, and Sean purposely playing The 1975 (because he knew it was Liv's favorite band) they both knew there could be something more. Liv remembers coming home from the beach trip and telling her grad school roommates about Sean, stating: "I'm gonna date him". And like most things Liv sets her mind to, because she's usually right, they did start dating in February 2021. Over the next 4 years, Liv and Sean shared many weekend adventures, traveled to Mexico, hiked hundreds of miles, got new jobs, moved in together, camped in Shenandoah 5 times, co-parented Liv's elderly black cat, moved again, and finally took an eventful trip to Montana. Liv had a hunch that this trip could end with a proposal. Before leaving for Montana, Kirsten asked Liv to describe her "dream engagement" to which she answered: "just the two of us in a field with some mountains in the background". Admittedly, Liv even went through Sean's suitcase to see if he just so happened to pack anything that resembled a ring box. Sean expected this and moved the ring to a safe location. On September 13th 2024, after frolicking in a field, with idyllic mountains gracing the background, Sean proposed just like Liv had described. It was perfect... and thankfully, she was right, again. The couple is excited to start their next great adventure together: marriage. They are so grateful for the love and support of their family and friends, and can't wait to celebrate their lifelong commitment to each other surrounded by their favorite people.

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