Bailey and Jacob grew up a town away from each other, and officially met while attending the same middle school in 2013. Bailey was in 7th grade, Jacob in 6th when they both decided to try out for the school play Wizard of Oz. A mutual friend, Jackson, who is one of Jacob's groomsmen, introduced the two, as he was also in the play. Bailey used to take Jacob's flip phone because she thought it was fun to text on, meanwhile Jacob would take Bailey's Iphone because he could play games on it during practice. Little did they know they would be engaged 10 years later.

In 2017, prom season came around, and Bailey really wanted to find a date to the prom. She attended chemistry first block of school always asking her chemistry partner who he thinks she should take to prom. One day, the lab partner asked Bailey, "What about Jacob Thomas?" The chemistry partner was Grady, another one of Jacob's groomsmen.

Bailey and Jacob started to reconnect at school, and Bailey used the yearbook as an excuse to talk to and see him, since she needed pictures of his baseball team. The prom was approaching quickly, and Bailey was leaving for Florida a few weeks later. Bailey decided she had to act quickly, especially after hearing another girl was going to ask him to prom. Bailey found some old baseballs and wrote on them until it spelled out P.R.O.M.? put them in a box and gave it to their English teacher to give to Jacob the day she flew out to Florida. Bailey anxiously waited for the facetime call from the class to see what Jacob's answer would be. Even though he was embarrassed in front of his entire class, he said yes. Caught off guard, Jacob knew he wanted to take Bailey on a date since he just committed to attending the prom with her. He took her on a hike up Snake Mountain in Addison Vermont as their first "date" even though they were only attending the prom as friends. Prom came around, they had a great time with friends and classmates.

Jacob took Bailey to the movies, and to Goodie's to get a creemee (that is what Vermonter's call soft serve ice cream). Jacob was ready to ask Bailey out on an official date, but knew Bailey was uncertain. Jacob accepted her decision, but told Bailey he would be ready if she changed her mind.

After many signs, prayers, and conversations with friends and family, Bailey decided she was being called to the one person who continued to give her butterflies, and who had the biggest smile on his face when they saw each other walking into school each day.

On June, 4th 2017, Jacob asked Bailey to be his girlfriend and she said yes.

The couple attended a few more proms, school dances, and sorority cocktails. They led middle schooler's at Younglife camp, and continued to be part of various churches. Bailey and Jacob have explored many mountains whether it be skiing, hiking, or camping. Took a few trips across the nation, and out of the country. They both have had a few career and college course changes. The two have made lots of memories with family and friends. They have met some new friends, and kept in touch with old friends. Most importantly, Bailey and Jacob have continued to love, learn, and grow each day.

Bailey graduated high school in 2018 and went to college, while Jacob finished high school and started working in VT. The couple did long distance until 2020 when they moved in with friends in NH, which is where they have continued to live, leading up to the day Jacob proposed.