Madeline's controlling and bossy behavior, including criticizing Jason's lateness and nagging him about small things, leads Jason to break up with her, saying she is too controlling and not spontaneous.

Madeline initially gets off on the wrong foot with Mike, but as they spend more time together, he encourages her to take risks and be adventurous, leading her to fall for him despite her initial intentions to win Jason back.

Harley convinces Madeline to go on the Niagara Falls trip alone after the breakup, effectively organizing a 'sistermoon,' and later gets hired as a photographer for another couple's wedding, which allows Madeline and Mike to have more one-on-one time.

Mike is actually an aspiring singer/songwriter who writes a song about Madeline for his open mic night, but he is devastated when Madeline stands him up, leading him to walk off the stage in heartbreak.

Jason reaches out to Madeline after seeing her social media posts, and they get engaged again, which betrays Mike and complicates Madeline's budding romance with him.