July 16, 2021 was the day Alex and Maddie officially met in person; however, it wasn't the first conversation they had. Three months prior, Alex and Maddie matched on the infamous dating app, Hinge, but after just a few messages, Alex GHOSTED Maddie and they never met until July. Maddie was having a night on the town with the girls and Alex was with his brothers downtown. At Press Pub, Maddie noticed Alex and told her friend, Bailey, but Alex was standing with another girl (who we later find out is married). After the girls left, Bailey messaged Alex and told him "her friend thought he was cute" and that he should come meet us out. Maddie thought Alex was with the married girl so didn't have any hope. Two hours later, Alex and his brothers walk into Wagon Wheel and Maddie noticed. She grabbed his arm and then said the most romantic words to win him over... "You're the guy that ghosted me." The rest is history.

They had their first official date the following Tuesday at Cazzy's Corner Grill. Sparks were flying the entire two-hour dinner. When Alex went to the bathroom, Maddie gave the waiter her credit card to pay for the date forgetting Alex's three cocktails and her $8/hour salary. But she liked him enough and wanted to make sure he knew it!

The proposal was a picture perfect day. Alex and Maddie went on a Gilliam Family Vacation on a Mediterranean cruise. From Cannes, France to Ajaccio, to Italy and Ibiza, the trip was sure to be one to remember. Alex told Maddie they would have some alone time the morning of their day in Italy. So, when they got off the train, Alex and Maddie first went to the bathroom (no public restrooms). Little did Maddie know Alex was taking the ring out of his bag and putting it into his back pocket. Alex then told Maddie he had mapped out a walking trail he had found online. Again, little did Maddie know this was planned with the hidden photographer. As they walked the path across the water, Alex recommended they stop and listen to the tour guide talk about the national park. When the tour guide finished and the group passed, Alex got down on a knee. Neither Maddie nor Alex remember the words, but both remember it being the best day of their lives to date. After the proposal, they had an hour long photo shoot in Cinque Terre, Manarola, Italy before celebrating over an Italian lunch with the family. The day was near perfect aside from running in the streets for a mile and a half and almost missing their last call on the cruise ship.