In January 2015, Dean invited Sarah to join him in Chicago for a trip to Second City. Sarah thought it was a group outing, but only Dean showed up with Starbucks hot chocolate for two when her train arrived downtown. They grabbed a drink at a local bar in Old Town and were both pleasantly surprised to see that they ordered the same stout. Sarah characteristically nursed her beer, then they rushed down the icy sidewalk - where Dean nearly fell several times - to Second City. They had such a good time that they've gone back every year since. After the show, they walked around aimlessly exploring the city on the cold, snowy night, until they ended up sitting down near the train station. They sat in the cold for what seemed like an hour in front of a group of ugly trees that neither will ever forget until it was time for Sarah to take the last train home. Though they sat on opposite ends of the freezing bench, they both later admitted knowing that this might have been more than just another trip into the city.

Sarah and Dean grew closer over their shared interests, including good food/beer, the Illini, music, nature and travel! They've cooked new recipes, experienced new restaurant week menus in Chicago and Philadelphia, and sampled craft beer from around the country. Combining their love of food and nature, in 2017 they even started their own community garden plot in Naperville and found creative ways to transform their mountain of zucchini and yellow squash into memorable meals. Their parents warned them that gardening together would truly test the strength of their relationship. They've listened to jazz sets in New York, Chicago, and New Orleans - Dean wholeheartedly supporting the saxophones and Sarah cheering loudest for the trombone solos. Their desire to hike and spend time together exploring nature has taken them across the country - from Glacier National Park to Savannah, Georgia and a few of Illinois' State Parks in between.

On January 19th, 2019, Sarah started her day with an unexpected text from Dean's grandpa that included a riddle. The answer sent Sarah and Dean to the train station - a place they often found themselves on Saturday mornings in preparation for a day trip downtown. Although Sarah was full of smiles and questions, Dean continued to deny any knowledge of what was going on and did what he does best...play dumb. That was the start of a day full of riddles from her sister, her college roommates, and some of her favorite Marching Illini. The answers took them across the city to spots and activities they had enjoyed together, including good food, good drinks, and good music. The last riddle took them back to the group of ugly trees where their first date ended almost four years ago to the day on a similarly cold and snowy night. With no one else in sight, Dean asked Sarah if she would spend the rest of her life with him and she said yes!