Cassie could be ready to take a chance on her feelings for Sam; Grace goes on a magical mission to fix a broken confidence.
Cassie goes a horseback-riding date with Sam, but John's exciting news keeps her caught between the two men's affections. At Grey House, guest Alexis finally admits to Cassie about her financial falling out from her father but promises to settle her bill. Cassie knows Alexis will follow through, despite George and Abigail suggesting harsher punishment. Eve fears Grace will replace her as Sam's receptionist, but Grace puts a plan in motion to help restore Eve's confidence.
Meanwhile, Sam worries Nick isn't ready to study abroad but an important job offer could make him reconsider. Stephanie receives an opportunity to move on from her heartbreak, only she realizes she deserves a second chance with Ben. As Cassie devises a plan to help Brandon and Tara agree on a change for their future, she gives Martha insight on helping her son.
However, after Cassie agrees to assist John with a new project at his university, she realizes their connection could impede her growing feelings for Sam. She must decide if that is a risk worth taking.