Toby was originally Ashley's study buddy when they were home schooled. Soon, they started hanging out a lot and texting just as much. In the Season 3 finale, they tell George, Ashley's dad, that they both took the GED and passed. They also say that they want to travel across America together, unsupervised. They also say that they want to get emancipated, and Toby says that his parents are okay with it. It is unknown if either he or Ashley get their wish on that one. They leave for their trip in the Season 4 premiere, and as of "When Opportunity Knocks", they are in Florida at his grandmother's house.
During their sessions, he tells Ashley that he has had sex twice. He said the first time, the girl ended up crying and then she told her mother, and her mother told his mother. This got him into a lot of trouble, even though it was her idea to have sex. The second time, a girl kept saying, "not like that," making him cry when he got home. He tells Ashley that he wants one normal sexual experience, and that he would love to have sex with her. Ashley tells him to give her one good reason why they should, and he tells her that she's prettier than Amy. Ashley brightens at that, and tells him that she'll sleep with him, but a second later she says that she was kidding.
It is confirmed by Ricky and Amy in the Season 4 premiere that they are dating.
In Season 5, Ashley leaves for Italy without Toby, after he refuses to join her. Later, he is saddened by her departure.