I am by no means a great photographer, but I do have a couple of tricks when it comes to shooting portraits that I thought I’d share. Here they are, in order of importance.

1. Never use a flash. Maybe “real” photographers with add-on flashes would disagree, but when I use the built in flash, I’m NEVER happy with the result.^(1)
2. Use a prime lens. I shoot with the Canon 50mm f/1.4 lens. It’s Canon’s middle of the road offering at about $400. Their entry level lens is the Canon 50mm f/1.8 lens at about $100. Their professional version is the Canon 50mm f/1.2 lens at a little over $1400.
3. Use the lowest f-stop possible. I shoot in aperture priority mode (Av on my Canon) and crank the f-stop all the way down to 1.4 (that’s the lowest my lens supports).^(2,3)
4. Get closer than comfortable. Not physically closer, but “zoomed in”. It might be because the lenses that I suggest are mild telephoto lenses, but I always feel like I’m “too close”, but in actuality that what you want. Your subject should be very pronounced.
5. Shoot just off center. I like to keep my subject just to the left or right of the center of the photo. You can do this by centering the subject, pressing the shutter button half way down until it beeps, this sets the focal distance, then move the camera slightly left or right and take your picture.

Footnotes

1. Bonus tip: related to “never use a flash”. Shoot 20 minutes before sunset or 20 minutes before sunrise if possible. The lighting is perfect. My friend Craig Deutsch taught me that one.
2. The lower the f-stop, the shorter the depth of field. The depth of field is the amount of the picture that’s in focus. That’s what gives the nice blurred foreground and background in the picture above, while keeping the face in focus.
3. Update : You may have noticed the lenses get exponentially more expensive the lower the f-stop. If you are interested, Stanley Kubrick used a f/0.7 lens when shooting Barry Lyndon … and it’s available for rent.