|Family||Charles Crews Sr. (fiancé)|
|Played By||Christina Hendricks|
Olivia has made repeated, and always rebuffed, attempts to make contact with Crews resulted in her spending a lot of time with Ted, who developed feelings for her. She gently turns down his romantic efforts while trying to maintain a friendship with him. Her relationship with Charles Sr. ultimately broke down when she couldn't take the strain of their poor relationship any longer.
- Olivia Canton was played by Christina Hendricks.