Andrea and Thiel met at a cookout in Baltimore in July of 2014. Andrea noticed him when she came in (and asked her friend about him lol), but it wasn't until it was time to play a game called "Heads Up" that the two actually spoke for the first time. From the moment she sat next to Thiel, the two talked for the remainder of the cookout. (At this point the “How We Met” story varies based on which person you ask. Thiel’s side: “I was eating a plate of wingettes and she was staring them down so I offered her one.” Andrea’s side: “I was minding my business enjoying the casual conversation, and he offered me some wingettes so I indulged.” To this day, both claim their version of this story is the truth). Thiel walked Andrea to her car that night, and the two exchanged numbers outside in the misty rain before parting ways. From then on, the pair continued a long distance relationship for the next two 1/2 years, traveling up and down i95 from Philly to Maryland until Thiel relocated to Maryland in 2017. Some of Andrea and Thiel's favorite things to do as a couple include finding the best brunch spots in the city, mentoring, concerts, and they also consider themselves forerunners of "Netflix and Chill" before it became a thing.

After praying on it, and getting the approval from the Dashiell family, Thiel was ready to ask for Andrea's hand in marriage. He knew he wanted it to be just the two of them and he wanted to re-create their first date. Thiel's best man was having a gender reveal in Philadelphia on Christmas Eve and Thiel knew it wouldn't raise any flags, stopping to get lunch along the way at the Baltimore Harbor. Thiel met with the manager of the Cheesecake Factory two days before the proposal to go through how the proposal was going to take place. He arranged for the couple to sit across from where they sat on their first date. Thiel knew Andrea was going to want a piece of chocolate cake, so he was going to have a piece of cake and the plate would read, "Will you marry me?". On the day of the proposal, the couple arrived at the Baltimore Harbor, Andrea stated, "Aww, we haven't been back here since our first date!” As the couple entered the Cheesecake Factory, Thiel gave the manager a head nod, and from that moment, the plan went into action. The couple sat across from the seats on their first date with a beautiful window view of the Baltimore Harbor. Ordered their food, had a great conversation and was ready for dessert. The waitress asked if Thiel and Andrea wanted any dessert and Andrea said, "No", she was full from the meal. Thiel encouraged her to get a slice of cake but she did not want anything. When Thiel stated he would like a piece of cake, Andrea stated she was baking cakes for Christmas and Thiel did not need back to back days of cake. After negotiating, Thiel decided to get a slice of carrot cake. In the four years of knowing each other, Andrea had never seen Thiel eat carrot cake. After what seemed like forever, the waitress final turned the corner with the carrot cake, Thiel stood up from his chair, dropped down on one knee (he stretched the morning before to make sure it would be smooth) and asked for Andrea to marry him. You guessed it, Andrea said, "YES"!