Eric tries to arrange a romantic evening with Annie, but Annie keeps turning down every attempt he throws at her. At the same time, Annie takes Eric by surprise with the news that she would like to quit college and to start teaching to help get her out of her depression. Meanwhile, Simon is at risk of being fired from his new job at the pizza parlor by his excessive tardiness and discovering that waiting tables takes more people skills than he's equipped to handle. Also, Robbie sets Lucy on a date with one of his friends while Matt is concerned about a woman who keeps showing up at the clinic a lot. Lastly, Mary performs terribly in fire fighting training distracted by her consuming relationship with Wilson.