Dear Poor Lucky Me,

I’m confused: Are you seriously going to the Taste of Chicago? 

I am a long time reader of your website…but this move goes against everything I thought I knew about you.

What do you hope to accomplish by attending this food fiasco?  Aren’t you worried about permanent physical and psychological affects?

With Concern and Affection,
You Don’t Have To Do This

Dear Y.D.H.T.D.T.,

Sincerely,
Poor Lucky Me

Dear Readers,

The decision has been made: Poor Lucky Me will be attending this year’s Taste of Chicago. It was not an easy decision to make considering that two of my most hated activities are standing around in a crush of fat people and eating standing up.

However I think that it’s high time to expose myself to some activities popular among the rest of society. Preliminary research shows that the public enjoys nibbling on a variety of fried novelty foods (turkey leg, candy bar, twinkie), staring at each other’s tattoos in jealousy and hoping that others are jealous of their own tattoos, and using porty-potties.

To prepare myself for the upcoming dive into The Taste, I have made the following adjustments:

1. I hastily gained 45 pounds. My heart pounds when I roll over in bed now, but it is important that I blend in with the other food-revelers.
2. I have cut down to one huge meal a day. To keep my stomach gaping and insatiable, I have eschewed breakfast and dinner for three weeks. Instead I eat a 5000 calories lunch that starts with chocolate chip pancakes and ends with a fifth of Jim Beam.
3. Elastic waist banded pants have replaced anything fitted in my wardrobe. I appreciate the gastronomical freedom these pants afford me.
4. All laced or slip on shoes are stored away and have been replaced by Crocs or flip flops. My toe nails are appropriately yellow and horny. Perfect for outdoor dining!
5. A bottle of Maalox is consumed each night before bed to coat and sooth my intestines.

I still have a lot of work to do, but I think I’m on the right track. My roommate is still trying to talk me out of bringing a weapon, but it seems like a pretty good idea so far. Please feel free to weigh in with your suggestions.

With Love,
Poor Lucky Me

Dear Poor Lucky Me,

I recently read an article in the Suntimes about a postal worker who rented a storage locker and stuffed it with the mail she was supposed to deliver. I feel like it would take a decent amount of time to bring the mail to the locker and those things aren’t cheap to rent- why not just go ahead and deliver it?

My mailman rarely gets the whole delivery right- my mailbox is usually stuffed with my neighbor’s mail, or I’ll get items ten days after they were sent. So, what’s the big deal? Why didn’t she just do a shoddy job like everyone else in America? No one is demanding perfection.

Additionally, I once heard that 10% of storage units contain a dead body. What do you think about that?

Best,
It’s All About Trying, Not Succeeding

Dear Not Succeeding,

Sincerely,
Poor Lucky Me

Dear Poor Lucky Me,
I work at a reputable law firm in a big city. Most of the people dress like regular business people…but there’s one attorney here who dresses like a whore. A classy whore, but a whore just the same.

The weirdest part is that she has very different looks. For instance, earlier this week I think she was dressed as one of the backup singers from that Robert Palmer video- slicked back hair, lipstick and all.

Today she’s wearing a skirt that is at least 3 inches above her knee, possibly more and I’m not positive you can’t see her cooch when she sits down.
Don’t get me wrong, I’d kill a squirrel for her legs, but still!

Am I uptight or is this lady desperate for attention?

Signed,
Nostalgic for a Little Modesty

Dear Nostalgic,

Sincerely,
Poor Lucky Me

Dear Poor Lucky Me,
I work in a small office building that is home to a variety of businesses, and one floor below our offices is a pole dancing school .

For several hours a day I hear thumping music from their classes, and all day long beautiful women walk in and out of their offices. What is the attraction to pole dancing classes? There can’t be that many women who want to be strippers in my city.

Also, one of my local watering holes has a small room off to the side with a dance pole.  When I queried the bartender she told me that mainly women use it, but late night a lot of drunk guys give it a whirl.

What gives?  Am I missing out on something?
Signed,
Private Dancer

Dear Private Dancer,
Let me assure you that there are more women in your city who secretly want to be strippers than you can ever imagine. While the internet is an incredible tool for communicating, researching, and entertaining, the proliferation of amateur porn has changed everything.

Sincerely,
Poor Lucky Me

I’m trying to get my Master’s Degree in the social implications of Whole Foods.  The interaction between the employees and patrons and their collective relationship to the products present a fascinating study in Douchebagology.

The employees are dreaded, tattooed hippies who openly resent the people shopping there and are hostile if asked for a plastic bag.  The average customer is an upscale, annoying yuppie with children in tow and/or talking loudly on a cell phone. 

How do these two groups co-exist in the same over-priced food store? Going there is like watching that video where the lion takes care of the gazelle baby, except the baby needs gazelle milk and you just know eventually the lion is going to get a hankering for baby gazelle meat.

You cannot shop at Whole Foods if you’re in a hurry.  Even if the aisles weren’t jammed with high-end baby carriages and recently tummy-tucked mothers, it’s nearly impossible to find anything.   I’m pretty sure the store layout was designed by highly intelligent apes who were taught how to use drafting software.  They did a decent job considering they aren’t human, but we’ve come to expect a little more when shopping for $3 tomatoes. 

The aisle design couldn’t make less sense, especially considering how many people who work there are probably stoned.  I always expect to find a lost, scared hippie having a freak out in the frozen food aisle because they can’t find their way back to the coffee section.

Hopefully my adviser will accept my dissertation idea, because I’ve already logged in hundreds of hours observing the animals in their natural habitat. I had a spy camera made out of a hemp necklace that i wear around the store while I stare at people ordering cheese.

I think people need to know that the problem is not them, it’s Whole Foods.

People throw around the expression “The Worst Thing I’ve Ever Seen” a lot, without really thinking.

Maybe you said it when you saw a disturbing documentary, or an hour you watched on the surgery channel. But nothing, absolutely nothing, could possibly be as horrifying and disheartening as the video below.

I washed my eyes and ears in bleach after I watched it, and still fear I’ll never be the same.

Dear Poor Lucky Me,

I just saw someone wearing a hat that was inscribed with the words “Natural-Born Hustler”. I’ve always dreamed of becoming a hustler, but I wasn’t born that way.

Do I have to give up my dream or is there still a chance for me?

Signed,

Born with a silver spoon in my mouth

Dear Born,

Well the good news for you is that no actual hustler would ever be caught dead in a hat like that.  In fact, you are more likely to be hustler than that guy just because you don’t own that hat.

While many hustlers are born that way, many more are made.  They can be victims of circumstance, low self esteem, misguided about what is cool, or just poseur douchebags.  50 Cent did more harm than good for the legitimate hustler community.  Drug dealers and pimps across the nation are doing desperate market research on new labels for themselves.

I just sat in on a consumer test board conducted by two gentlemen who ran a gambling and human trafficking ring.  They wanted our opinions on the titles “Monee Mkr” and “Ho Bagger”.  It’s sort of sad, really, that hardened street toughs have to resort to such mainstream behavior to find another word for their alternative lifestyle.

In short, you have plenty of time to buy a hat or tee-shirt that labels you as a hustler.  You don’t have as much time to recruit a stable of hoes to slang ass for you, but you can do anything you put your mind to.

Sincerely,

Poor Lucky Me

Hello, and thank you for inquiring into Prison Camp!

Our two week retreat in the upper Upper Peninsula will prepare you for any real world prison situation that you might encounter.

In these tough economic times, one can’t be sure what’s around the corner; armed robbery, securities fraud, drug dealing, prostitution.  Any number of crimes might be tried on for size to help supplement one’s dwindling income or unemployment check. Because the chances of an amateur criminal not getting caught are so slim, doesn’t it make sense to arm yourself (no pun intended!) with practical knowledge that can help you survive- even escape- your prison sentence?

Prison Camp was founded in September 2008 by Chuckles D.*, Ross Fineberg, and Fat Baby Johnson.  All three have had extensive experience in the justice system, and wanted to find a way to share their knowledge with the inevitable next wave of petty, violent, and white collar criminals.

*Please note that we ask you not to make direct eye contact with Chuckles for your own safety.

During your two week stay you will learn such life saving skills as:

How to make a shank out of a toothbrush.

What gang to join based on your ethnicity and penchant towards violence

How to dig a tunnel with a plastic spoon

How to keep your street clothes dry while swimming through a culvert or sewer

Shower safety

In-cell fermentation techniques

In-cell tattoo techniques

How to give yourself a nickname that doesn’t make you sound like a bitch

And so much more!

The last day of camp will be a mock prison yard fight.  You will be able to put your new skill to work!  The winning gang will be treated to a banquet and a list of unscrupulous lawyers who are awaiting your call for help.  Or to assist in facilitating an identity change.  Scalding one’s finger prints off will be a small additional charge.

We are so looking forward to spending time with you this summer, and hope you’ll call or email with any questions!

Dear Poor Lucky Me,

I have been to several movies where people (assholes) come in late to the movie and then ask other people to move around so the late people can sit with their whole posse in one big happy group.

Am I crazy to think this is ludicrous behavior on two fronts: First, why do you HAVE to sit next to your friends during a movie?  Isn’t the point of going to a movie to focus on the movie and pay attention to the action on the screen?  Why is a solo theater excursion frowned upon socially?

And second, how big of an asshole do you have to be to come late to a movie and then ask people who are seated and comfortable to move around so you can sit with your group?  Really, show up 15 minutes earlier and everyone in your group can sit together and not talk to one another the whole movie.

Wait…A third and related question is -why don’t more people tell the groups coming in late and asking people to move to “Eff off”?  Shouldn’t this sort of rude behavior demand some kind of social shame and ridicule?

Please help,
Theater Fury

Dear Theater Fury,

Sincerely,
Poor Lucky Me