Madison and Jeff aren't your typical High School sweethearts...
They didn’t date until after they graduated. And even though they had the same friends, they didn’t really interact with each other until Jeff decided to ask Madison to Prom their senior year. But once they started talking, they never really stopped. They dated the whole summer after graduation and both wanted to keep dating into college, even though they were going to different schools (Jeff to Baylor and Madison to Texas). After 4 (LONG) years of long-distance dating, they finally moved back to Dallas to live in the same city full time and to start their careers.
Jeff and Madison had known for a long time that they wanted to marry each other. To keep the element of surprise, Jeff made sure to drop LOTS of hints that an engagement wouldn’t happen until Spring of 2018. Since the engagement was actually planned for the Saturday after Thanksgiving, Jeff had a lot to plan and less time to plan it. He called Madison’s dad and invited him to a dinner to have “the talk”. After getting his approval (and filming a spoof version of asking for his permission), they had to rally the troops together for the planned engagement party.
On the day of the engagement, Jeff was “playing golf” with a couple of family members. In reality, he was powerwashing the backyard with his dad to prepare for the party. Madison was supposed to come over to Jeff’s apartment to ride together to his sister’s place for cocktails before a family dinner she was “hosting”.
Not knowing what the night had in store for her, Madison wasn’t exactly in the biggest hurry getting over to his apartment. Madison was leisurely getting ready while watching Taylor Swift music videos with her mom in the hopes she would have a better chance of getting tickets to Taylor’s concert (she did get her tickets). Her mom was trying to play it cool and not rush her, but she was very concerned that Madison had not left yet. She became more anxious when Madison started asking for outfit advice; this is not something that she usually does. In reality Madison just couldn’t decide on what shoes to wear with her new top, but everyone else was concerned she knew something.
Jeff was getting worried about time, since his plans involved their photographer, already waiting in the park and a race to get photos taken before sunset. In an effort to push Madison in more of a hurry, Jeff called his sister and had her text Madison asking if they were heading over soon to “have cocktails”. Madison finally got a move on and was on her way. He met Madison in the parking garage and said they should head straight to his sister’s place to see if they could help set up for the “dinner” that was never actually going to happen.
In the car ride there, Jeff asked her to open his glove box. He had asked Madison’s family members to write her letters of why they were thankful for her as a “Thanksgiving surprise”, which is definitely not a normal thing. But Jeff made sure to lower Madison’s expectations about the letters telling her “It’s not THAT surprise” and “I don’t want you to be disappointed” in an effort to throw her off, or at least confuse her for the short car ride.
After the reading of the letters, Jeff drove them to a park where his guitar was set up to sing to her. A couple of happy tears and wonderful photos later, they were off to his parent’s house for the after party of family and friends!