Womanizer Don Draper isn't afraid of an affair with a client or a client's wife, but he should be. By doing so he's risking the loss of clients and accounts, not to mention his company and family finding out about his indiscretions.
Lesson learned: Mixing business with pleasure can get very dicey! Set professional boundaries and talk to HR if you start up a personal relationship with someone you met through work.
Photo courtesy of AMC