Daisy and Matthew finally went on a date after a week of unfortunate events that kept causing the date to be rescheduled. Matthew took her on a private helicopter tour, by the end of the date Daisy ended up getting a kiss and the keys for Espinoz's Porsche to joyride.
After pulling her over for a traffic stop a few days later, Espinoz offered to watch movies and cuddle at his house, which Daisy has yet to respond to. While Daisy thinks Espinoz is a nice guy, she is developing strong feelings for Bailey Jade and is hesitant to continue seeing Espinoz.
In the first few meetings of each other, they noticed that they both wore the same black pocket shirt, it's almost like they were meant to be soulmates... In the early stages when Daisy and Bailey were just getting to know each other, it was abruptly interrupted when Bailey was suddenly a contestant for a dating show that Daisy was a Bachelorette for. Bailey ended up winning and won a date for her and Daisy at Zee Nanakaze's restaurant. This ended up negatively affecting their relationship since it made things between them more awkward and put pressure on their relationship progression.
They eventually end up going on a date but on their own terms. Daisy took Bailey out scuba diving at Chumash Pier, they dived together and swam with dolphins. They had a picnic on the beach and watched the sunset. Their conversation was as rough as the waves, and Daisy unfortunately had to end the date shortly due to unrelated issues.
After talking and dealing with miscommunications, they both agreed that the date was awkward due to the pressure of others and labeling it as a date, even though they hang out often. Over a number of weeks, they have been hanging out casually whenever they can and getting to know each other, smoothing out any awkwardness between them. They became very protective of each other and call any of their matching clothes stupid. On December 3rd, 2019, Daisy asked Bailey to be her girlfriend and they became an official couple. As a Christmas gift, Bailey surprised Daisy with her dream car, a 1966 Ford Mustang Fastback. Their relationship has earned the nickname #Dailey.
Following over a year of dating, Daisy and Bailey broke up in December 2020. Daisy felt that it was time, and that she and Bailey had grown apart. Daisy is convinced Bailey will be better off with someone else in her life.
One of her best friends, they did news together for a while, and he used his brilliant wing-man skills to help bring Dailey together by encouraging Daisy to go on a date with Bailey.
