|First appearance||"Are You Being Observed?" (19.01)|
|Guest appearances||18.07, 18.09, 18.10, 18.13, 18.16, 18.17, 18.18, 18.20, 18.21, 18.22|
Almost ten years after her final appearance in Crane Life, a rebellious, 15-year old Hester unexpectedly follows her brother David to Bear Creek midway through Season 18, following an argument with her parents about her new boyfriend. David agrees to watch out for her, becoming her effective caregiver when Niles and Daphne emigrate to China on business. Hester is quick to assert her independence, enrolling in a local high-school and getting a part-time job in the club's hire shop as Svetlana's assistant. Hester graduates high-school at the end of Season 20, but elects to remain in Washington with Maris' motley crew. After she and her colleagues quit Bear Creek at the end of Season 22, Hester sublets Maris' swanky townhouse in Season 23. Later, when Maris sells the townhouse to move onto an estate in Toronto, Hester opts to join David in moving to Canada with her.
In Season 20, Hester begins dating Gregory Ryland, the rich, privileged son of a local hotel heiress, though it quickly falters when Gregory is revealed to be pumping her for information to assist in his mother's adoption case against Maris. Hester makes amends with a repentant Gregory later in the season, and attends her high-school prom with him. By Season 21, their relationship has fallen apart once again after Gregory, now beset by financial concerns, dumps Hester to pursue a relationship with a rich girl. In the season finale, Gregory returns to Bear Creek to marry his new girlfriend, but flees the wedding ceremony when it is learnt that his mother Shirley arranged the marriage to lay the groundwork for a future business deal. Hester subsequently elopes to Vegas with Gregory, returning to the club in Season 22 as a newly married woman.