Dan and Lauren met on Poipu beach in Kauai, brought together by the magic (and convenient pick-up-line) of a sea turtle. Since Lauren had just "crushed a couple tacos," she did not take Dan up on his offer to use his snorkel gear to go see said sea turtle. Instead, they had a casual conversation about the meaning of life and what each other was passionate about. Lauren shared that she lived in the LA area and learned that Dan lived in a suburb just outside Chicago. They left without exchanging contact information, but given Lauren's expert online detective skills, they ended up connecting on LinkedIn. The two continued to get to know one another over FaceTime coffee dates. Dan then took a leap of faith and flew out to LA to visit Lauren, but his best friend Kirtan kept tabs to make sure Dan didn’t go missing. They shared oysters and drinks in Santa Monica, hiked in Malibu, fed the army of ground squirrels off Ocean Avenue, and braved the freezing Pacific ocean. They continued their adventures in Tahoe, Denver, Asheville, and finally, Chicago. They hiked, flew kites, ate oysters, drank Bloody Mary's, drove scooters, played yahtzee, sang karaoke, and enjoyed the magic of Chicago’s summer boating on the lake and exploring the city. Lauren had always wanted to live somewhere with seasons and things fell into place and led her to Chicago. Dan’s family and friends graciously welcomed Lauren into their lives and made her transition to a new city seamless and so much fun. The couple visited Lauren’s friends and family in LA and Las Vegas, where Dan was met with rave reviews and approval. Dan helped Lauren learn about winter, and taught her how to sail, ski, and be a Bears fan. Lauren got Dan into acupuncture and gardening, and turned him into a cat person with the help of Holly.

At the end of January, Dan planned a staycation in the city where he popped the question. The day started at the aquarium with a sea turtle and continued onto Navy Pier. Dan had tickets for the ferris wheel and planned to propose while overlooking the city, but when they arrived for the reservation, the ferris wheel was shut down (that witchy Chicago weather). Dan didn’t understand why no one reached out to let him know, and Lauren didn’t understand why Dan was so adamant about going on this ferris wheel. They continued on with the evening and Dan came up with an exciting idea to walk out to the end of the pier. Lauren was less enthused and provided a counteroffer to stay inside where it was not dark and cold. However, she sensed Dan’s eagerness and decided to sacrifice for the person she loved. It was out there on Navy Pier, with the waves crashing and the glow of the city and moonlight, that Dan got down on one knee and Lauren said yes to a lifetime of adventures.