We follow perpetually-single Will as he attempts to woo women, while avoiding any real commitment. His life changes when a quirky, bohemian, vegan single mother, Fiona, and her 11-year-old son, Marcus, move in next door. Marcus is a misfit, and already being bullied at his new school, yet he and Will strike up an odd-couple friendship, under Fiona’s disapproving watch.

Marcus asks Will for advice on how to get invited to a girl's birthday party.

Fiona gets dating advice from Dakota.

Marcus is cast as Romeo by a new teacher in a school production featuring Shakespeare scenes.

Feeling nervous about her first real date with Mr. Chris, Fiona wants Dakota to come with her as her safety net. Will ends up tagging along as well as he attempts to woo Dakota.

To celebrate a year of friendship, Marcus convinces Will to take him to the Golden Gate FemFest. Meanwhile, Dakota helps Fiona prepare for a night of intimacy with Chris.