Jessica and Dillon met each other on a dating app the summer of 2014, right after Jessica graduated from college. Since they had some mutual friends, Jessica thought it couldn’t hurt to take Dillon up on meeting in person. They went out on a couple of dates and liked each other, but the timing wasn't right. They went their seperate ways but remained on eachothers radar being connected on social media throughout the years. Finally in July of 2019, the stars aligned! Jessica and Dillon were both single and matched on a dating app AGAIN. Jessica thought before their (2nd) first date, “wouldn’t it be funny if I married this guy?”

Right before Jessica’s 30th birthday, Dillon asked if we wanted his brother and sister-in-law’s dinner reservations that they “couldn’t make at the last minute.” It was a Sunday night, but Dillon knew Jessica was always down for a good meal. Off to Brooklyn they went, Jessica not suspecting a thing. 8 delicious courses later, they were enjoying dessert. Only having a few tables in the pop-up backyard restaurant, Chef Jay went around checking in with the guests often. He told Jessica and Dillon he was sending over an extra dessert, which obviously got her very excited. All of a sudden, the whole kitchen staff emerged walking towards them with sparklers. She’s confused, at first thinking they must be celebrating her birthday. She was shocked when she noticed there was a ring on the plate! Once she processed what was happening, she immediately said YES! The icing on the cake was that Dillon had both of their families waiting back at the apartment to surprise her with (more) dessert and lots of decorations.