Ilana Gershon discusses how we all have moments in which someone’s use of new media baffles us, and we have to ask a friend how to respond. It often isn’t just the content of the message, it is also using that particular medium in that way which leaves us scratching our heads. In this talk, I discuss what anthropological concepts can help us understand our confusion. I will turn to LinkedIn as my case study and analyze the dilemmas people face when using LinkedIn as they look for a job. This will be my starting point to discuss how the newness of new media generates social dilemmas, especially for the people these days who are looking for a job.