At the University of Michigan, Josh and Lindsay both joined the pre-law fraternity Kappa Alpha Pi (KAPi). They met in the fall of 2015 when Lindsay joined, and immediately were drawn to each other. But, it wasn’t until a full year later - in December of 2016 - that their romantic relationship began. Josh asked Lindsay to his fraternity date party, she accepted, and the rest is history. When Lindsay graduated in 2017, they proceeded to date long distance for five years [though Josh likes to correct that it was technically only 4 years and 11 months of long distance]. During those 5 years, Lindsay spent the whole time in NYC, and Josh spent 1 year finishing Michigan, 3 years in law school in Boston, and 1 year in Chicago. In 2020, Josh spent 5 months in quarantine at the Hurwitz house in Baltimore, and solidified his place in the Hurwitz clan. Lindsay finally moved to Chicago in the spring of 2022, and Josh proposed on April 16, 2023.

On Sunday morning, April 16, Lindsay was woken up by 8 of her best friends who had flown to Chicago from all over the country. After several minutes of "what's happening!?", the girls had a bagel brunch that Josh had set up and helped Lindsay get ready for a day of more surprises to come. At 10:30, Lindsay was given a card from Josh with a love letter and clue in it to the first stop of what would be an incredible scavenger hunt. When Lindsay left the house for the first stop, she saw a limo that Josh had sent just for her. Her friends sent her off to the first stop of the scavenger hunt - the theater where Josh and Lindsay had seen Hamilton in 2017 during their first trip together to Chicago. Upon arriving, Lindsay was excitedly greeted by her family, who handed her yet another letter and clue from Josh. The Hurwitzes piled into the limo and set off for the second stop - Josh and Lindsay's first apartment together. Waiting there were the Martins with another letter and clue from Josh as well as a bouquet of Hydrangeas (Grandma Hurwitz's favorite). They hopped in the limo and accompanied Lindsay to the last stop - North Avenue Beach. At the beach, the Martins and Hurwitzes were instructed to walk Lindsay 3/4 of the way to Josh, who was impatiently waiting at the Chess Pavilion. Josh proposed alongside a violinist playing their song - "All My Lovin" by The Beatles, and Lindsay ecstatically said YES! Lindsay and Josh's family and friends then came running over - they'd been waiting in the rain to celebrate with the happy couple! Many tears and happy screams later, they all went to an engagement party down the street from Lindsay and Josh's apartment.