Jack and Bailey first met...
...in Corpus Christi at work. Bailey was working as an office manager and Jack was one of the vendors. He delivered goods to her workplace for a month or two and he would always ask Bailey what there was to do in Corpus. Bailey noticed that Jack was always very polite. Bailey's best friend noticed (and insisted) that Jack was interested in Bailey, however Bailey just thought that Jack was being professional by creating small talk. This continued for several weeks until one day he was in his truck and asked Bailey if he could take her to do dinner. Bailey told him that he could IF, and only if, he could remember her phone number and she shouted her number to him as he sat in his truck.
Bailey did not expect Jack to remember her phone number. He was sitting in his truck and she shouted it to him rather than writing it down for him or allowing him to write it down. But Jack did remember her number! He sent Bailey a text about an hour later which said, "You owe me dinner ma'am."
That same evening Bailey replied to Jack's message and told him that she was caught up at work and would not be able to make time for dinner with him, even though she was actually at home.
The following week Jack showed up to deliver goods at Bailey's workplace and he asked her if she would make time for dinner with him. Again, Bailey said that she would. However this time she actually did go to dinner with him. They drove to three different places before finding a restaurant with good customer service. They enjoyed dinner and laughed...a lot!
Over the next few months they continued talking casually. One weekend Bailey decided to travel with Jack for a weekend trip to visit his parents. They met his parents at Texas Roadhouse (THEIR place to eat) and then went to the family ranch, where Jack showed Bailey around. Jack had Bailey put on some torn up dirty overalls and they began working on the ranch. Bailey had a great time! It was completely different than her life in Arizona.
Eventually Jack asked Bailey to move in with him and ever since they have been inseparable.
One day Jack surprised Bailey…
with a shopping trip for a fancy dress. Jack would not tell Bailey why she needed the fancy dress. The next day Jack told Bailey that they were going to dinner that night and she had to be ready at 5:00 sharp...and she HAD to wear the new fancy dress. Bailey joked about dressing up for dinner at Texas Roadhouse! Jack laughed and told her to get ready.
At 5:00 Jack told Bailey that it was time to go and she headed to the garage as she normally did. Jack told her to just use the front door. After all, "It's easier," he said. Bailey questioned Jack about this as she walked out the front door and saw a limo waiting for them. Bailey was so excited and began to get tears in her eyes. They enjoyed the limo ride to Del Friscos Steakhouse in Houston, a beautiful restaurant with an amazing view. They enjoyed a delicious dinner, even though Bailey noticed that Jack was acting...different. Jack told her that he loved her and would continue to love her forever and he would do everything he had to in order to give their family a good life. He went on to say that it was not the right time to get married because they weren't stable enough yet, but he just wanted her to know that she was his world.
When they finished their meals, they decided to order dessert. Bailey ordered cheesecake since that is their favorite dessert. Jack left to the restroom and was gone for awhile. When he returned Bailey told him that she didn't know it took 20 minutes to bring out dessert. About this same time the dessert arrived...and it said, "Will you marry me?" Bailey began to panic because she was sure that the waiter brought them the wrong plate! She looked at Jack to tell him how embarrassing it was that they brought the wrong plate to their table and saw Jack on one knee with a ring. Bailey jumped into his arms as she cried and said, "YES!" She gave him her right hand instead of her left hand!
You can read more about Jack and Bailey’s engagement here.