1) Location Location Location. Scout out a cute place to situate your subject -- this could be a neighborhood coffee shop, your living room, a sumptuous garden or a textured wall. The environment will appear slightly within the frame, but most important, the space will be comfortable or uncomfortable for your subject. Where would they feel best, prettiest, most relaxed? Go there!
2) Get your subject interacting with a task, object or movement. It's so much easier to create a beautiful, natural portrait without the subject staring directly into your lens. When the blogger is at her laptop or chef at his kitchen table, there's material for them to connect with and look at ease. You can crop out most of the activity and your subject will look relaxed and beautiful.
3) Lower the F-Stop (into the the realm between 1.8-5.6 depending on your lens/body). Shooting "wide open" with a very shallow depth of field keeps the subject sharp and the background soft. This contrast will pull the subject forward and emphasize them. It's a quick device to get to a pretty photo of a person.
4) Keep dialogue light. Chat up your friend/subject, get them giggling. Saying things like "Work it, honey!" can produce the laugh and in that moment, you can create beautiful head shots.
5) Get weird in a photo booth! Maybe you don't need to be there at all as the photographer . . . Is there an old photo booth in your city? Depending on the subject's needs, it's always a cost-effective, stylish alternative to a full blow shoot. (Images: Leela Cyd Ross)