Big cities are some of the best places for people-watching! Check out our exclusive bi-weekly column on the fabulous people of Chicago.

Do boys ever become men?

October is always a ladies month in my mind. I mean the city lights in Chicago are pink for breast cancer awareness — even NFL players are wearing pink shoes and gloves in tribute.

Get Guilty Gurl

Get Guilty Gurl

No matter how tempted I might be to initiate sarcastic banter with the innocent, I’m better off sticking to People Watching than People Talking — also known as conversations.

The Loop Ness Monster

The Loop at lunch is pretty much the same every day.

The V Party

With a craving for chicken and waffles, sweet tea, and a burger and fries from Merlotte’s – I, Caitlin, am addicted to True Blood. If I don’t catch up on these seasons soon, I may be unable to people watch again.


Starbucks is a people-watching heaven, and last week I remembered what it was like to be in retail hell.

My Little Monsters

The thing about people watching at Lolla is that — well– I guess it’s that because there are so many people to look at or so many people who tried to look bizarre — it all kind of cancels out and becomes this entirely over stimulating mess.

The Joni Mitchell Punk Movement

I get pretty bummed when I forget my headphones in the morning. A mistake like that rules out Groovesharking all day and listening to music on my commutes. However, it does amp up my listening and people watching skills and the only thing better than people watching is eavesdropping.

Morning Routines

Your morning routine is probably something you take for granted every day, but maybe stop and look around next time. You may notice someone who will change the way you look at your day.

Breaking News: The Stanley Cup Came Out at the Gay Pride Parade

The gay pride parade in Chicago is certainly a day full of color, energy, and incredible people watching.

She and Him and Her and Me

Summer things are happening in Chicago. And you know what that means… excellent people watching!

Oil Spill in the Loop

Commenting on the behavior of our fellow Chicagoans is one of my favorite pastimes. Check out my bi-weekly people watching column!

Eyjafjallajökull in the Spring

Watching Chicagoans is one of my favorite pastimes. Especially in the spring. Check out the first installment of my people watching column.

My Love Affair with a Man Named People Watching

I love looking at myself in “The Bean” just as much as the next tourist, but what I love even more is going to “The Bean” and watching other people look at themselves. Check out my bi-weekly people watching column for my latest observations on Chicagoans.