Like bird watching - only not at all.

One of the upsides to living in a large metropolitan area is People Watching. Major cities provide People Watching greatness at a level rivaled only by airports. Thing is, after living in a city for so long, you become desensitized to most of the amazing things you encounter on a daily basis. It's only when I am with people from out of town that I realize how much I ignore my surroundings. I will be power-walking my way down the street, expertly navigating the sidewalk cracks, hell-on-heels grates and unidentified piles of nasty - all while sending an e-mail and simultaneously telling my friend about the “crazy day” I just had at the office. At the crux of my titillating tale, I will inadvertently realize that I have lost my friend…to some homeless dude.

(Note to people from outside of big cities: When someone who appears as though they have not showered in a few years inquires to whether they may ask you a question – keep walking. If you are a slave to etiquette, you may politely say” no.” However, if they begin to follow you, keep walking. Do not make eye contact, do not slow down. Do not pass go, do not give the man $2. This is not because the person might hurt you (though I wouldn't rule that out), but rather, because this person is banking that they will annoy you into giving them money – more money for those of you that give him the $2. Forget your manners and keep walking…besides, if you stop to talk to Captain Crappedhispants, you will miss the best part of my awesome story.)

I don’t want to lose my friends to homeless dudes, but I also don’t want them (or me) to miss out on some prime People Watching opportunities. You just have to know how to do it right. Your first order of business is to find a good place to be. The middle of the sidewalk is not a good place to be. Think of People Watching like any other activity. It's better if you find an appropriate location. I mean, sure, I could take a crap while I walk around and stare at skyscrapers, but wouldn’t it be better (and ultimately more pleasant) if I just took the time to find proper facilities? Location is everything, baby. For People Watching, benches, grassy areas, and leaning against the side of a building are all excellent options. However, if the weather is nice, consider sidewalk seating at an outdoor café. That way, you can eat and converse about your sightings.

Next, talk about what you see. If we are People Watching and you see a group of people with no pants…you better point that out. Better yet, make a game out of your People Watching experiences. Below are some of my favorites;

1. Guess the Occupation: Just as it sounds - as people walk by, try to figure out what they do for a living. Make it fun. Is the short guy in the brown loafers a salesman or a gigolo? He may really be a sales guy, but wouldn’t it be cooler if that incoming call was from a woman desperate to pay for what’s underneath his Dockers? Nice pants, indeed.

2. Turn it into a drinking game: This obviously works best from an outdoor café or a friend’s balcony. Every time you see some douche with one of those Bluetooth headsets – drink. Drink twice if he is yelling at the person on the other end of the line. Take a shot for every cab driver that freaks out.

3. Gay or Foreign: This is one that can even be played while walking. Fashion can be tricky. Consider the following photo example and ask yourself…is that dude gay or foreign?

This is a game I often play with my gay friends. It's amazing how "Gaydar" flies right out the window once a European accent negates the fashion cues. I also especially enjoy this particular game. The same guy could be perceived many different ways depending on fashion choice. Again, consider the following photo example;

In a suit, the guy looks great. Fashionable and ready for an event. This look is very "now" and neither the guy's sexuality nor nationality are really peaking my curiosity. He may look a little too Ashton Kutcher-ish for my taste, but that's besides the point. It's not like I'd kick him out of bed or anything.

Same guy in the 70's print button up and hat? Totally foreign. I can hear the accent now. He would never dress this way at home, but he is visiting a foreign city and was mislead by window displays. Feeling as though he may not be able to attract American women in a t-shirt and jeans, this guy was lead astray by an overzealous hourly employee at a designer resale shop. With an American accent - total d-bag. But now peekture heem wiss moor oov a frawnch acceent. Kinda do-able, no?

In the third outfit - totally gay.

See how fun this can be?