After weeks of texting, FaceTime, and anxiously waiting to meet one another in person, Maddie came home from Illinois State University for the weekend and it was finally time for their first date! Danny picked Maddie up from her house and off they went to enjoy dinner and drinks. Right off the bat Danny knew the way to Maddie's heart after revealing he had bought them tickets for a Haunted House - one of the best in the area! They talked and flirted for hours while waiting in line and held one another tight as they navigated through ghouls and goblins. The date came to an end when Danny drove Maddie home, and they sealed the night with a kiss!

Danny and Maddie were supposed to travel to Ireland where he had an elaborate and detailed plan to create a dream vacation that would conclude with a proposal. However, due to the unforeseen pandemic, it would be up to Danny to come up with an alternative idea and fast! The vacation was rescheduled for Salem, Massachusetts. With the help and support from Maddie's sister and brother in-law, Molly and Nick, Danny knew he could still pull off the perfect proposal. Prior to the big day, the two spent their time exploring the autumn festivities Salem had to offer and even got to go whale watching off the coast of Cape Cod. When the day had finally arrived, Danny proposed to Maddie on Castle Hill at The Crane Estate where they were immersed in the beauty of dewy fall leaves, rolling hills, and moss-covered statues frozen in time. Danny, Maddie, Molly, and Nick went off to celebrate the new engagement by enjoying dinner and champagne sea side, accompanied by the most perfect sunset.