Will had been planning the engagement for awhile. They've both known they were meant to be together since the beginning. Will had plans to propose when the two went on a mini vacation to Tampa to see the Orioles and the Cubs play at Tropicana Field. However, the jeweler that was making the ring, broke his arm and did not finish the ring in time for Will to pick it up before the trip.

Will was then going back to Knoxville to play in the annual Father's Day golf tournament. Emily and Will made date night plans for the night he got back to have dinner at the Polynesian Resort and watch the Magic Kingdom fireworks from the beach. Emily even thought to herself she could be assisting in planning her own engagement. Emily didn't realize that Will couldn't wait another minute to propose. When Will got home from work before date night, he asked "Do you want an i love you gift before we go to dinner?" Emily had been napping on the couch and confused, got up and said yes. Will told Emily to wait in the bedroom while he got it and when Emily came out of the bedroom, Will was on one knee with the ring and Pearl and asked, "Do you want to go to Disney as a fiancee?" Emily was still in pajamas, hair wasn't done, and no make up on, but the moment was perfect. They called their families, who had known it has happening for awhile now, and got ready and went to dinner and enjoyed the fireworks.

Registry