Bailey and Dalton first met on the Franciscan University of Steubenville's Men's Basketball team. After harassing the head coach for weeks in order to become a team manager, Bailey was finally accepted under the terms in which she set (i.e., that she wasn't joining the team to date anyone). Fastforward a couple months, into the climatic year of 2020, and Bailey was fatefully introduced to Dalton on January 2nd, wooing him over with, and I quote, "her orange shorts and curly hair." Little did Bailey know what she was getting into by joining the team. It took over a month of constant advances on Dalton's behalf before she began to wonder if Dalton was, "giving her vibes." (Or, more realistically, she finally began to believe what everyone was telling her since Dalton and Bailey first met.)
If it wasn't already obvious, as the split dates indicate above, the date in which Dalton and Bailey first "went out" differs depending on who you are talking to. In Dalton's eyes, the first "date" was a result of a failed bowling attempt a few days before January 30th in which Dalton and Bailey decided to go to a local bar in Steubenville with friends. It was there that Dalton began to acquire feelings for Bailey due to her ability to communicate and get along with him (a feat which most people find impossible) and he then made the correctly calculated move of spilling beer on Bailey's jeans. A deed which obviously could only make Bailey like Dalton more. Then, on the other hand, Bailey first recognized the fact that Dalton and she were dating after showing up to an end-of-the-season party together and verbally confirmed to the team they were "officially" dating. Thus, fulfilling her contract with the head coach of the basketball team by waiting till after the season.
"The Proposal." Never has a word conveyed its true meaning in a more significant way than when Dalton decided to "beg" Bailey to marry him. Set in his ways, Dalton began his pursuit of matrimony by balancing the terms in which Bailey set for him regarding how he was supposed to go about the matter. You see, Bailey explicitly told Dalton that she desired not to be proposed to on All Hallows Eve. One, because she apparently had some deep dark history to the date, and secondly, because she didn't want to dress up. Knowing his limits, Dalton did what any sane man wishing to win over his potential wife would do. He hedged his bets and did everything she told him not to do. Not only did Dalton propose to Bailey on Halloween, but he also bought them tickets to go to the local Renaissance fair in the hopes that she would be forced to dress up. She didn't, but they went all the same. The proposal on the other hand, was conducted at a quote-unquote, "Kitten Cafe," where Dalton bribed the already suspecting Bailey with her favorite entities and food (kittens and burgers). And with that, who knows where these kookie kids will go in the future, but together they are unstoppable.