Barbara and Stan's first forays into the dating scene ends up differently than they anticipated. Stan is taken aback when a pretty female colleague flirts with him and ultimately ends up asking her out. Barbara, meanwhile, joins an Internet dating service and arranges a meeting with one of her matches. As the two prepare to go on their dates, Barbara tries to undermine Stan's confidence while she builds up her own. Meanwhile, Karly interferes in Winston's dating life causing a mix-up that almost costs her a job she loves.