On St. Patrick's Day 2017, Shannon received an email from her boss "Are you free for a business trip tomorrow in Monterey?" With nothing on her schedule, Shannon replied "Yes!" and started planning. She felt bad telling Jason since he often talked about driving up the coast and spending a weekend together in the seaside town. Jason was very supportive, and the next morning Shannon kissed him goodbye and boarded a plane to Sacramento. Shannon's boss, Jen, worked remotely from the capital, and she met her at the airport and drove them 3 hours down to Monterey. By the time they reached the town, their meeting had been pushed an hour or two, so Jen decided to take them on the 17 Mile Drive, a picturesque, meandering road in Pebble Beach. They stopped and took photos along the way, and enjoyed the idyllic beaches and views. Jen mentioned that she really wanted to see the Lone Cypress Tree, a well-known landmark along the drive. When they arrived, they walked down the staircase to a platform with a view of the tree overlooking the ocean. A few other people were there as well, and a golden dog caught Shannon's eye. She thought, "that looks like my dog," then quickly realized that WAS her dog! She looked up and saw Jason standing there. For a split second, Shannon was worried Jason crashed her business trip, but Jason took her hands, and said, "You didn't think we'd let you see Monterey without us, did you?" He shared a few other sweet sentiments that neither of them can remember, followed by "You know I'll love you forever, right?" Then he got down one knee and popped the question. Later, Jason revealed how we planned the whole thing. There was no business trip (Jen was in on it as well) and he and Hollywood rented a convertible and drove up the coast after Shannon left for the airport. Jason, Shannon and Hollywood spent the next two days celebrating in Monterey then took a beautiful drive back down the coast to L.A.