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This is a topic I can really relate to.
With my disability I am often forced to observe life from the sidelines, although those of you who know me, or have just read my stories will know that I've lived as much of my life as possible centre stage, but people watching has for many years been a part of my life.
I've always found that you see people at their best or at least most entertaining when they are at leisure. Weather on holiday, at festivals, sitting around in pubs or bars, or just walking about.
I have to admit, and i feel confident that I'm not alone here, that the 'beautiful young things are the best to watch'. Whether this is a problem or not depends a lot on who you are with. If you are with a partner who for some reason is just not confident in your relationship, they can find your people watching very worrying, simply because of their own insecurity. If however the opposite case applies you can have great fun observing and commenting on people with your partner.
Of course watching people when you're with a good friend is worry free, you can laugh, criticise, gasp, lust and generally say whatever you like about the people you're watching, and of course two pairs of eyes are better than one, and you can draw each others attention to any little piece of behavior or glimpse of accidentally exposed piece of flesh worthy of observation.
I once had a buddy who made  an art out of glimpsing what was meant to be concealed, he called it 'Blimping'
However often or for whatever reason you like to people watch, it is a fascinating and often pleasantly surprising pastime.
AlmostAristotle AlmostAristotle 61-65, M 6 Responses Apr 30, 2011

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Hey free. Thanks for the comment. You could have used it as a post in this group it was very interesting.

I too like to watch people. Sitting on an open terrace or coffee shop in the mall. I imagine what the passers by are going through there background and daily routines. I look at there faces and the way they are dressed to get some idea of there backgrounds. The young and fresh once are like flowers in the garden. The immature teenager warring there mismatched clothing and rebellious outfits, some show to much skin some to much make up all very interesting. Then there is the lady in amongst them walking regally amongst the peasants. Well groomed and dressed to perfection, wishing she was somewhere ells. My wife before we where married thought that I was not interested in her and that I was eyeing up all the girls in the shopping centres. Now she knows that I look with loving interested eyes not lustful once she is at ease and also not insecure any more in our relationship. Unfortunately she does not share my passion for the tapestry of life that unfolds and moves around you. It is for me as interesting as looking at art in a museum. It is living art at its best. Every person is a creator and artist even if they think they are not they all work on there body and paint there daily picture. I love looking at people from all walks of life. I often go to Cabramatta a suburb of Sydney (Australia) over the last thirty years is inundated by Vietnamese people. The place is a hustle and bustle of many different cultures and people the smells shouts characters it is a wonderful place to visit and people watch. I am glad I am not the only one in this world that has this passion.

I know what you mean Nz :)

I know what you mean about smiling at frowny ppl. When I'm out and about I try consciously to keep a little grin on my chops, as though I have an amusing little secret. 'enigmatic'?

Hubs and I are both people watchers and when we're out and about, we can keep each other very entertained with our observations. NOT making fun of folks either, sometimes we just sit and make up, "might be" scenarios of who they are, what they're thinking or where they might be going. It's a great way to pass time waiting at the airport or even when you have to be stuck on line somewhere.<br />
It's fun. <br />
I also love to smile at "frowny" people. When their face lights up in a big old grin, I feel soooo good! It's like a personal gift from them to me.

I agree there is so much pleasure in people watching. It is even more enjoyable when you have good, open-minded company to share your thoughts with. I know that while people watching could be construed as judgmental but I think it is human nature to have "opinions". I LOVE PEOPLE WATCHING!