peterg Loc: Santa Rosa, CA

You are not alone. There are lots of on-line tutorials. Google for them. Find and practice the techniques that you like. A few of mine:
Some cameras emit lights when focusing, self-timers, etc. I cover these with black tape so they don't attract attention.
Start with a smartphone, which attracts less attention.
After picking your subject, pretend you're shooting something else. Then, smoothly swing to your subject, snap the shot and continue panning... and keep looking through the viewfinder. The subject may not realize that you got a picture of them.

Hip Coyote

A few random thoughts. I travel quite bit and gravitate towards photographing interesting people. I try to find out the customs of the locals in case they want a small amount of money for my taking photos. I NEVER take photos of homeless or people who are obviously in distress. I try to talk to my subjects and show them the photo I took. With regard to not taking a camera in bars, I disagree. In many places pubs are THE cultural focal point of the area. Once walking into a pub on an Irish island and found about 50 kids playing Irish flutes as part of a cultural event. One girl got coaxed into dancing. It was wonderful. I abandoned photos and took video which I almost never do.

I don’t like telephoto shooting. Usually shoot a wide prime.

People are friendly all over the world. Just talk to them.

AzPicLady Loc: Behind the camera!

I understand. I don't like to ASK because then the person ceases their absorption in what they were doing and the shot is gone. If I don't ask, then I'm intruding. So I tend to avoid people altogether. Sometimes when they are quite far away or perhaps isolated I include them for scope. Or because their presence adds to the scene. But seldom.

BlueMorel Loc: Southwest Michigan

My son doesn't want me to post photos of him without permission. Ok by me, so I dont. I was conditioned not to bother people so I could never be a street photographer. But I do take pics at festivals and other events, just not for sale. I did have to assure a preschool teacher once that i was at a lake park to take park pics, and that i wouldnt take pics of the kids in her care.

Hershel Loc: New York City

I tend to gravitate to doing mostly Street Photography and a fair amount of photography at the Coney Island Boardwalk/Beach. While I am not overly timid or shy I have no desire to ask any of the many people in my photos whether I can take their picture as they are all in a public place. To this end I always make sure to have a long zoom as I most frequently shoot in the 300-600 mm range (35 mm equivalent) and that solves the problem. As I am tired of schlepping around 2 lenses, I'm now experimenting with the Sony RX10 IV which has a fixed 24 mm- 600 mm fixed zoom lens which for me is all the coverage I need at both end of the zoom range.

HERSHEL

ToBoldlyGo Loc: London U.K.

Still think it's best to make sure they're happy being the subject of a photo.

Just Shoot Me Loc: Ithaca, NY

I found that anyone who realizes they are in a shot either ignores me or they come up to me and give me their E-mail address and ask to have me send them a copy. I do.
Usually not a problem. These days you and I are on cameras everywhere we go. Stores, parking lots, banks, you name it.

Spectre Loc: Bothell, Washington

I sometimes just keep my camera at my waist and trigger the camera from there. Using a wide profile capture and cropping the photo afterwards. This works fine at times that you don’t want to be obvious. 📸

19104 Loc: Philadelphia

no its not ridiculous at all, I love doing street Photography and have done it for years. but I was away from it got a while and getting back into it, I realized that I am much more timid than I used to be.
back in the film days what I would do using a wide angle lens is pre focus and stop the lens down to like F8. And just take pictures and keep moving. The other thing is that a lot of people at public outdoor events
feel that they have a right to privacy, when in reality they do not.

John

OddJobber Loc: Portland, OR

I frequently take cameras into my local bar, rather than leave them on the street in a two-seat convertible with no secure storage. If I have a suitable lens I'll take a few snaps of the patrons, and it's rare that anyone objects. (After all, they're already on 8 security cameras. )

Chico 1948 Loc: Cincinnati

I am new to modern DSLR and have a D7000, D750, and a Lumix DMC-FZ300. I shot with a Konica C35 while in Vietnam and a Canon A1 before going digital. I use the Lumix for street work. It has a 25-600 mm Leica zoom lens that works great and the articulated LCD monitor helps in being a little discreet. I never take photos of children I don't know unless a parent asks me to. Practice makes street photography easier.

Pete

was_a_guru

Many years ago I saw an ad for a right angle mirror attachment for the end of a lens. I believe it screwed into the threads of the lens (where a filter would go). You would, for example, point your camera north but would be taking pictures to the west. Never bought one, but that would be a good way to go for secretly photographing people.

chasgroh Loc: Buena Park, CA

...me too! This and the "phantom" subject. But sometimes I find a person who's so interesting I just have to approach him/her and engage in some conversation...the end of that dialogue is usually, "...ok, I'm not going to take your picture now but will be back when you least expect it." Never a problem, and some of these subjects might be down on their luck so I sweeten the pot, so to speak...

DJCard Loc: Northern Kentucky

I second that emotion. Street photography is a lot of fun for me when in America and other countries. I just try to be as polite and invisible as I can with my big, highly visible DSLR!

Pixie Jackie Loc: New Hampshire seacoast

When people are out in public, they're fair game. You don't have to ask permission. However, to be truly "candid", you try to catch people unaware. I found that my best "people" candids were when I used my Mamiya 645. It's a waist-level camera so you can pre-focus, roam around and look down into the viewfinder and when you find something interesting, you can shoot--- usually without the people even realizing that their picture has been taken. (Some say "stolen" but I don't agree. If they're out in public, it's O.K.) What really makes people uncomfortable is to have you roaming around, putting your camera up and down to look through the viewfinder. Then you're a dead give-away. Unfortunately, the Mamiya 645 uses film--and because it was a larger format than 35mm, it used 120 or 220 film. That was great when I had a darkroom--the B & W candids were nice and sharp. (Although I processed slide film as well.) But now I'd have to find someone to develop the film and make prints for me.
Not as satisfying since you can't crop in an enlarger, etc. -- Jackie