Jenna and Simon’s story begins, as all good teen rom-com movies do, in high school. As freshmen, both Jenna and Simon joined the policy debate team at Dowling Catholic High School. As the two navigated their new school and new life, it became (painfully) obvious to all that Simon was obsessed with Jenna. Unfortunately, being fourteen and an idiot, Simon didn’t know how to handle this. His (many, many) attempts to “subtly” woo Jenna were predictably horrible. For several months, Jenna (rightfully) spurned his advances and mocked his attempts at suaveness. Eventually, Simon decided it was time to move on (although clearly not fully). With Simon’s foolish attempts at courting Jenna out of the way, the two started to develop a real friendship. Through hours on buses to debate tournaments and even more time backstage waiting for practice to start, they began to get along. Slowly, Jenna began to act a little differently around him and drop hints everywhere. Soon, it was obvious to everyone but Simon what was next.

Though he was no longer fourteen, he was still an idiot. Sure that Jenna would never change her mind, he continued in his life blissfully unaware of what he was missing. It took mutual friend (and bridesmaid) Kristina Maude repeatedly hitting him over the head for Simon to realize what was happening. For their first date, they went to see the re-release of Disney’s The Lion King. A few days later, with a long walk down the “500” hallway at Dowling Catholic (in which Jenna interrupted him several times) Simon asked Jenna to be his girlfriend and she responded with a resounding “sure.” The two dated for two years of high school before facing the daunting prospect of college. Simon accepted a scholarship to debate for Baylor University in Waco, Texas while Jenna accepted a scholarship of her own to debate for Gonzaga University in Spokane, Washington. Though they knew it wouldn’t be easy, the two decided to do their best to persevere through 4 years of living almost 2,000 miles and 2 time zones apart. They saw each other every month and a half or so thanks to similar debate schedules (though, thankfully, they never had to actually debate one another). Jenna graduated early in December of 2016 and decided to stay in Spokane and work. Simon took his full four years and graduated in May of 2017. After one last summer apart, the two moved to College Park, Maryland to pursue graduate studies at the University of Maryland – Jenna studying for her Masters of Public Policy which she received in May of 2019, and Simon working towards a PhD in Political Science which he will receive in 2022 (hopefully!). Living in the same city again was everything the two had hoped it would be.

The next step was for Simon to get his act together and propose. However, after a previous debacle with a jeweler (also thanks to bridesmaid Kristina Maude), he was hesitant to take on ring shopping by himself again. Luckily, Jenna didn’t trust him to pick out a ring that she would wear for the rest of he life without help, so she agreed to go along with him “just to look.” She found a ring she loved and told Simon to get one “like that one.” Not trusting himself not to screw it up, Simon instead selected that exact ring. While the ring was being made and shipped, Simon (with a little help from Bridesmaid Sonia Schulte and sister Colette Sheaff) planned a proposal. After seeing the movie Black Panther (5 Stars!) and a nice dinner, Simon drove Jenna to a patio with two sculptures near it – both are a part of a series that also has an installment in the Pappajohn Sculpture Garden in Des Moines. Since Jenna and Simon both love Des Moines so much, it was a beautiful way to tie in the city that means a lot to both of them. With fairy lights surrounding the patio and the song “Can You Feel the Love Tonight” from The Lion King playing, Simon got down on one knee and asked Jenna to marry him. She responded with a resounding “sure.”