Well first off, I'm shooting with a Pentax K10D, which is a 10.2 megapixel camera that I got used for about $399 of Craigslist. I go with Pentax cause I'm not paying for a brand name.
The lens I'm using is a Tamron (again, cheap, but fairly good quality stuff) 28-75mm f/2.8. It is by far my favorite portrait lens out of the other two lenses I have....... (50mm f/1.4, and the Pentax kit 18-55mm)
Now I don't exactly remember what settings I had it on, but here's how I figure it out. If I'm not trying to capture a fast action, or blur an object moving fast than I'm not going to adjust shutter speed first. Since I didn't really like the way my front door and the hall to the stairs looked behind my head, I used f/2.8 as my aperture (wide open). That way the door and hallway will blur into the colors of the wall, which were white, and you'll get this nice smooth grey like a backdrop. A low aperture and a far background is a good way to get rid of busy or ugly scenery. It was also pretty dark in my living room, but since I had my flash I guess that doesn't matter. When I connect my flash up to my camera (I used a flash extension chord, I'm not exactly wireless) my camera can't use shutter speeds over 1/180th a second, and since my flash is only emitting light for that length of time, that's as long as I need it open anyways.
If my face is too bright or too dark, I can do one of two things: 1) move the flash closer or farther away from my face, or 2) turn up or down the ISO on my camera. I like to keep it at 100, but I'll go as high as 560. You'll start getting noise around 400, so careful. My face was too dark at first, but I wanted to keep the lowest ISO as possible, so I moved the flash closer to my face.
You'll notice that the light on my face is very smooth, it doesn't look like the flash from the camera your mom uses at birthday parties that sits in the drawer with the pens all year. There's two reasons for that. The first is that I have it off-camera. It's moved camera left and raised a little bit. Not too much, but enough to not be straight on. In your normal life, you never strap a light to your head and look at people. I don't know why they ever did it for cameras... The second reason it looks nice, and this is the smooth reason, is because I have it shooting through a beauty dish. Familiarize yourself with the DIY beauty dish link, cause I'm going to keep talking about it. I have a 14" beauty dish, which was about a foot or two away from my face. The top of the bowl was above my hair and the bottom of the bowl was the same height as my chin, and it expanded the width of my head, as my head is not 14" wide... So you can imagine, if light is bouncing into the bowl and being sent back out of it, that the light is pretty diffused. This explains the softness of the light, and why beauty dishes are called what they are. Cause I'm freakin' gorgeous in this picture. No photoshop. (Juuuuuuuuuust kidding....)
The self-portrait above, however, is just one flash, and I did this because I had thrown on my button down shirt and tie, and my cardigan, and I was kind of in a hurry cause I didn't want my roommate coming home and catching me. Not that I post it all over the internet, but it's just weird when you're taking the pictures. It's like doing a video blog in front of your mom.
I'm usually not into "meaning" behind art, I'll usually just make it really really really ridiculously good looking. I'm trying to be a fashion photographer. The "bigger picture" is printing it 13"x19". This one is different though. I did add meaning into this, and symbolism.