Model Gabriella Brooks marks Healy's longest girlfriend, with their relationship spanning four years. In August 2019, The Sun reported that Brooks broke things off with the musician due to his partying. "He parties a lot at home when he's there and Gabby had just had enough. She doesn't want to lead her life like that," a source told the outlet at the time.
Healy appeared to echo the same reasoning for their breakup, telling The Guardian in a 2020 interview: "My 20s was fuck*ng chaos and I didn't live a domestic life so there are lots of things I've just not learned. I'm not emotionally very mature." He continued: "There have been times when it does damage my relationship and I ask myself: 'Why do I value my career so much?' I'm trying to relinquish that idea. I want to have a period in my life when I'm not conflicted about it."
The model has since found a new love in Miley Cyrus's ex-boyfriend Liam Hemsworth, whom she began dating shortly after the end of her and Healy's relationship.