Both piercers warned that cheek piercings are not the easiest piercings to heal. In fact, although there are piercers out there who do them safely and correctly, Beall and Gottschalk said these aren't piercings they typically do. "They sometimes don't ever heal," said Gottschalk, adding that if you're looking to get your cheeks pierced, they may be prone to abscesses and swelling. That being said, he estimated that a healthy cheek piercing could fully heal within 12 to 18 months.