Tim asked Priscilla to a date at City Winery, which was a new hip winery in Ivy City (and happened to be less than 5 minutes from his house). Priscilla and Tim bonded over their shared love of travel and joked about travelling the world on an airplane-super-yacht (sorry, Tim, I haven't found one yet). They clicked right away and decided to meet up again. Several rounds of minigolf (Tim won), TopGolf (Priscilla won), and a burnt vegetarian lasagna later they decided to date. Tim asked Priscilla to officially be his girlfriend on her birthday by bringing her roses at her door after a whirlwind date the night before of going to a jazz club and a fancy dinner at Georgetown. It felt like it was out of a John Hughes movie.
Priscilla and Tim were on a trip to Portugal for Tim's birthday. Priscilla was convinced Tim was not going to propose on the trip because it was "too perfect." The day after his birthday, Tim proposed in Porto at sunset overlooking the city. He had been planting the seeds of a perfect evening throughout the day ("let's go watch the sunset" and "let's go out for a nice dinner"), and timed his proposal to be almost at sunset (he got a little nervous). He started with "I had a great birthday with you yesterday, but there is one more thing I want" before getting down on one knee, with "Fly Me to the Moon" playing in the background. It was a perfect moment, and Priscilla said yes with happy tears. Luckily a nearby couple noticed the moment and took some pictures like the one above.