Choosing a Location
Find a crowded street cafe. Cafes are a classic people-watching destination. Many people visit coffee shops and outdoor bars/restaurants, and there will almost always be something interesting going on at these destinations. Cafes tend to draw both locals and tourists, giving you an interesting blend of people and personalities. Many people think of cafes as an excellent meeting place to get together and hold conversations. You can eavesdrop on what people are saying and gather fascinating (and true) stories from people's lives. If it's cold or wet outside you can people watch inside a cafe, but cafes with outdoor patios let you surround yourself with conversations while also witnessing strangers pass by on the street.
Choose a park bench. Parks tend to draw a lot of people, especially in large urban areas. Visiting a park offers an escape from the hectic nature of city life, providing city dwellers with a serene, natural environment. People tend to feel relaxed in parks, which makes a park a great place to watch people interact when they feel most comfortable. Though a park may have intermittent moments of silence, it will most likely have steady waves of people passing through over time. Parks tend to draw people of all demographics: the young, middle-aged, and elderly, families and single people alike.
Visit a bustling tourist attraction. Tourist attractions tend to draw people who visit from all over the world, yet they also draw a large number of locals. People are often hurrying to and from the various tourist attractions in a given city, so it can create a bustling, energetic atmosphere that is great for watching or even interacting with strangers. Take note of the things people photograph at a given tourist attraction. You may even want to spark up a conversation with tourists, asking questions like, "What drew you to this location in the city, and what does it mean to you?" Tourist attractions tend to have a steady stream of people entering and leaving, which means that if you sit or walk around for any length of time you'll see a perpetually-changing crowd of people.
Explore an urban square or plaza. In older cities, the square or plaza was an historic gathering place for locals to meet and exchange ideas or commerce. Today urban squares/plazas tend to be little parks, or simply an open space within the city. A square or plaza is an excellent place to watch locals rushing to or from work on their lunch breaks, as well as visitors from out of town who are trying to take in the city. If you live in an urban area, any square or plaza in your city will most likely be bustling and crowded, especially during work hours on weekdays and mornings/afternoons on weekends.
Go to a pedestrian street. Pedestrian streets (also called pedestrian malls) are stretches of city streets that have been closed to vehicular traffic. Some are temporary/intermittent pedestrian streets, while others are closed to vehicles all of the time. Pedestrian streets are usually lined with cafes, bars/restaurants, and little shops. These types of locations tend to draw a lot of traffic, whether people are visiting specific locations or simply taking in the environment (like you). Don't be surprised if you see a lot of other people watchers on a pedestrian street. If you don't live near a pedestrian street, you can try your local mall. Malls foster a similar atmosphere and tend to draw a lot of people.
Ride public transportation. For some people, public transportation naturally encourages conversations and interactions. If you're lost or unsure of which connecting subway line you'll need, you would naturally ask someone who knows the city. Public transportation offers a perpetually-shifting demographic of the city's residents and tourists alike. Most people enter and leave public transportation based on their neighborhoods and their destinations. By noting where the most people exit a subway or bus, you can get a good idea of which parts of the city hold the most common destinations.
Deciding How to People Watch
Walk around extensively. Some of the earliest people watchers walked extensively across their cities. Many of these flâneurs were writers and artists seeking inspiration by observing people, while others simply found pleasure in taking in the faces and wardrobes that were encountered. Walking gives you the advantage of an ever-changing crowd of people to watch, coupled with the changing scenery and atmospheres as you walk from one neighborhood to the next. Walking may be more ideal for people-watching destinations like urban plazas or tourist attractions. People watching while you walk can help you get some exercise, enjoy a little fresh air, and see parts of the community that you might not otherwise visit.
Sit in one place. If walking isn't an option, or if you get tired while exploring the city on foot, you can always sit and watch people pass you by. The advantage of sitting is that you still experience a constant stream of passersby while being able to take it in more fully. If you are sitting while you people watch, it's easier to take photographs or jot notes on the people you see. People watching while sitting is much easier than walking if you're interested in experiencing a city's cafes, bars/restaurants, or public transportation.
Look distracted. One risk of people watching is that others will notice you. If you're just walking around a city this shouldn't be a problem, but some people fear being watched by others, and may ask you what you're doing. For this reason, if you plan on sitting while people watching, you may want to look distracted in some capacity so that others do not feel threatened or uncomfortable. Try drinking coffee or a cocktail at a cafe or bar. If you're sitting outside, glance down periodically at an open book or newspaper to look like you have no interest in what people are saying or doing around you. Many people like to take notes or draw, based on the people and things they see and hear. If you have a notebook that's fine, but typing on a laptop or in your mobile phone's note-taking application can help you remain discreet.
Be appropriate. There are places and people that you should not watch, such as daycare centers, schools, and government buildings. Standing around watching people at these types of locations may arise suspicion, and someone may call the police. Make sure you are not in a "no loitering" area, or the police might be watching you. Stay away from private property, and instead stick to public spaces. If someone asks you to leave or tells you that you're making them uncomfortable, be respectful and apologize, then walk away. Respect people's privacy and their personal space. Don't be intrusive, and don't get up close to others unless you're moving through a crowded area and it is unavoidable. Never photograph someone without getting that individual's permission first.
Learning About Others Through Watching
Take note of identity. One of the easiest things to learn about others from people watching is how certain individuals identify themselves. Clothing is rarely ever just clothes; most people use their clothing to convey a certain image, a particular style, or to identify as a member of a culture or subculture. Sports merchandise suggests a strong affiliation with that team's city, region, university, or country. Look for jerseys, caps, or t-shirts and try to identify what a given team represents to that individual. T-shirts or sewn-on patches of a band's logo let you know that that person listens to that band's music and identifies with the scene they represent. Any band might print t-shirts, but patches are often associated with grunge and punk rock. Designer brand clothing indicates that fashion is important to that individual. These individuals may or may not be wealthy, but it's safe to assume that these people put a lot of thought into how they dress. Souvenir shirts and hats tell you where a person has been, whether the individual likes to travel, and what things are important in that person's social life (for example, Disneyland shirts might imply an emphasis on family). Tattoos may honor a loved one (in which case family is important to them), a military squadron (national pride and duty), or a city's skyline (home or a place identified as home). Try to interpret how a tattoo might represent that person's identity.
Make inferences about self-esteem. In addition to style of dress, you can learn a great deal about a person by how that individual carries himself or herself. Look at a person's posture, the way that individual walks, and the way he or she interacts with (or avoids) other people on the street to determine how confident or shy a person is, as well as how kind or selfish that individual might be. Good posture with a straight back and shoulders pushed back implies that a person is very strong and secure. This person may or may not be smiling, but is certainly confident in himself/herself at the moment. If you see someone slouched over and staring at the ground to avoid eye contact, or looking back over his/her shoulder, that individual is probably very insecure or self-doubting. There's nothing wrong with looking good, of course, but being perfectly groomed and manicured, as well as stopping to look in every mirror, are the common marks of vanity.
Guess at people's emotional states. Determining someone's emotional state without actually interacting with that person entails a bit more guess work than inferring that individual's self esteem or identity. There is no universal guide to emotions, as some people laugh when they are stressed out or cry when they are happy. However, generally speaking, you can make an educated guess about someone's emotional state by the way that person behaves in public. Anxious people tend to fidget, shrug shoulders, and look around nervously. Someone who looks sad or is crying is most likely sad or depressed, though again, you can't be certain without interacting with a person. A furrowed brow and/or narrow eyes usually implies anger or frustration. An individual who walks briskly and has some indication of a smile on his or her face is probably happy or having a good day.
Draw conclusions about people's personalities. You can tell a lot about a person's general personality traits based on the way that person moves through his or her environment. The easiest things to spot might be kindness versus selfishness, but there are many other facets of a person's personality that become evident if you watch for long enough. A kind, caring person will let you pass ahead, or will hold a door open for strangers. Someone who sees another person coming but lets the door close in that person's face is probably not a particularly nice individual (though that person may just be running late or impatient). Someone who makes eye contact with others and smiles is probably a very friendly, outgoing individual. By contrast, someone who makes eye contact while maintaining a cold demeanor may have an unfriendly or gruff personality. You can learn just as much about a person by his/her interactions with others as you can from someone's reluctance to interact with others. Take note of the ways people interact with or avoid one another, whether they're together in a group or strangers passing by one another.
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