Kendra was an assistant to Andrew Misher, a movie executive. Jonah Miller was referred to her by Charlie Kitsis. After Misher wanted to change everything in Jonah's movie script, Kendra stepped in and told him she wanted to make it a feature film on Jonah's terms.
After learning that she and Jonah had several things in common, she asked Jonah out and he accepted, despite being engaged. He later broke the date, however, though he failed to mention his engagement. After a fight with Riley, he showed up to their meeting spot and joined her out of anger.
They kissed, but when Kendra found out he was engaged, she ended the date.