They rekindle their romance in season two after she helps him cope with the discovery that he is adopted. They eventually split up because Ryan is headed to college while Tessa is still in Chatswin to finish her senior year. However, they reunite once again when he returns home for his father's funeral. In season five, it is revealed that Tessa and Ryan got married before he left for war. When he returns home from war, they divorce but remain friends. Tessa even dates one of Ryan's friends, Jeff, during this time but nothing serious develops between them. In season six, Tessa realizes she has feelings for Ryan again when he saves her life. They begin a relationship once more but it doesn't last long due to Tessa wanting to go to Stanford University instead of going to Columbia University like he does. However, they remain friends. In season seven, Tessa starts working at Stan's office as an assistant to one of its founders, Sean Parker. She soon learns that Ryan is running for mayor and tells him that she wants to run for city council but he says that he doesn't want her to. After losing the election, Tessa decides to stay in Chatswin and work at Stan's while Ryan goes back to school. However, they both return to Chatswin when he wins another mayoral race.