When Jay knew they would be in Orlando for a visit with his family, he knew that would be the perfect time to propose. He decided it would take place in front of Cinderella's Castle. I mean, Elyse is more often than not referred to as "princess" by her father, Chuck, so it makes perfect sense! Nathan, Elyse's brother was on ring detail all day while Jay waited for the perfect time to POP the question. A plan was concocted to distract Elyse while Jay got down on one knee. She had no idea it was coming. 14 family members were there to see the magical moment, and the rest, as they say....is history.