Attractive Person Faces Adversity – Tuesday November 17th

mickeyrourke30Poor Lucky Me,


There’s nothing “dear” about me or my story, so I’ll spare us both the formalities.  Mine’s a story heard all too often and never with a happy ending.  The headlong rush toward self-destruction and romance too often taken through a bottle of whiskey and a dash false-modesty sometimes culminates in a protracted custody battle, right? 


But unprotected sex aside, how do you suggest an arrogant sonofabitch, such as myself ever find his way back toward romance.  I’m in love with the product of my foolhardy actions; he’s a smart and funny boy cuter than I ever was or will be and twice as empathetic. 


The pity part isn’t the tens of thousands washed down the drain of an unforgiving legal system and the angry alley cat on the other side; the real tragedy is that I’m still in love with myself and haven’t got a self-reflective bone in my body. 


Short of a bone marrow transplant what do you suggest?


Unfortunately Handsome


Dear Unfortunately Handsome,
I feel that I can address you as such because it’s obvious that we share the kinship of devastating good looks. Indeed. You and I have special qualities that other people cannot deny, ignore, or help but envy.


People like us must triumph over a (usually alcohol fueled) series of bad choices and achieve great successes by failing upwards. It makes regular looking people have faith that they too can make something out of lives. Look at Mickey Rourke for god’s sake!


Self-Reflection might seems like a good idea but there’s a nasty side that people don’t really talk about: it can make you feel bad about yourself. And that’s the pits. But, then you can brag to people about what great perspective you have, and how in tune you are with your emotions. And that’s good. So it’s challenging.


I think you can find romance in the person who appreciates you for exactly who you are. Find someone with whom you share a mutual love and admiration for you. You’ll have something in common right off the bat.


Poor Luck Me

List! – Monday November 16th

cooldry-basketball-uniform127Ten Things That Can Make Your Pants Tight Other Than Weight Gain:


1. Water retention.


2. Washing pants in hot water.


3. Accidently putting pants on over another pair of pants.


4. Swimming in pants.


5. Using a vengeful dry cleaner.


6. Wearing giant underpants.


7. Using pants to store business papers and junk mail.


8. Leaving your basketball uniform on underneath pants.


9. Eating Chinese food twice in one day (this may lead to weight gain but will definitely lead to tight pants.)


10. Storing all you blood and guts right under the surface of your skin so you can make more room in your torso for muscles thus heightening your physical power.

Picture Day- Friday November 13th



This is a picture of one of my heroes, Yngwie Malmsteen. He is awesome, as you can plainly see from this photograph. If you don’t believe me, check out this video of him changing the world.



Mass Email Jokes Not Funny- Thursday November 12th

Dear Poor Lucky Me,


About once a month I will get an email “joke” from an old friend that I haven’t spoken with, seen, or even emailed in years. This email will contain nothing other than a forwarded joke and will include me and a handful of other people. The joke is never funny, not geared towards me and gives no clue as to what the sender would like in return.


Is this person trying to reconnect with me? If so, why not personalize the email?


Is the person super bored, so bored in fact that they went through their address book and found their most dormant contacts?


What gives?


Deleting Without Reading


Dear D.W.R.,
The Internet provides so many fascinating insights into weirdos. Just think: before the Internet we had little idea who was a pervert, a racist, or a religious freak.


I think that the person sending you email jokes is just trying to tell you they’re thinking of you. Or, they are a diabolical Lex Luther type and know how much their emails get under your skin.


A personalized email takes way more work then pressing forward, and brings you no good luck or riches like chain emails do. I can’t tell you how rich and powerful I have gotten from forwarding emails. The Bentley I drive, in fact, showed up in my parking space after I forwarded an Angel email. It was totally worth it.


Next time some one sends you a chain or joke email, why don’t you rely: “Thank you so much for the hilarious joke. I have forwarded it to 30 people. I expect untold riches for doing so and will hold you personally responsible if they don’t appear.” or you could just say “Thanks for the email! Thinking of you too.”


Poor Lucky Me

Patriotic Panhandlers – Wednesday November 11th

Dear Poor Lucky Me


On my way into work this morning I walked by two different “Uncle Sam Bums”. Both of these guys were holding signs like the one pictured above. Like the gentleman in the picture, both of these guys were in their 20’s.


My question is two-fold. How crazy can you be if you have the capacity to get a costume together to beg? Isn’t the funny-bum shtick the right of older, crazy bums like the guy that says “I won’t lie, I want money for booze”?


Yours Truly,
Please Help Me Out


Dear Please help Me Out,
I’m so over the guys who say “I won’t lie, I want money for booze” That is like the oldest gag in the book. Instead of giving money to those guys, I yell “Get some fresh material”. I like to give money to street musicians, guys who pretend the Onion is Streetwise, and veterans. It is Veteran’s Day, so maybe they were just reminding people to honor our veterans.


I don’t think you have to be crazy to be a street person- it helps but it’s not a requirement. You can just be a drug addict or an alcoholic which wouldn’t necessarily restrict your costume-making-abilities. You have to be savvy to score and if dressing up as Uncle Sam helps, then you’ve gotta go for it.


I try not to be judgmental about young homeless people, especially in Chicago. If you are 20 years old and can’t get your resources together to be a homeless guy in California or Florida, you must be in some serious trouble. I mean anyone could be a homeless person in Santa Monica- it’s not like you have to be tough. I’ve threatened to adopt that lifestyle several times. Me and my dog could hitch a ride to Cali and spend our days basking in the sun and eating canned beans. Seems like a pretty sweet deal. But if you’re working the street in Chicago, costume or not, you’re probably deep in the shit.


Poor Lucky Me

Reader Loves Tall Bikes, Loathes Others – Tuesday November 10th

Dear Poor Lucky Me,


I have a question for you – what’s with bikers? Seriously? What The Hell? In particular, I’d like your opinion on two specific qualities cyclists in Chicago all share in common, both of which I find infuriating:


1. All bicycle riders share an unveiled hatred for drivers, regardless of their driving ability


2. All bicycle riders share an unwillingness to comply with traffic laws, signs, signals and lights, and find automobiles’ strict adherence to these societal customs to be the primary source for their driver-hatred (see #1).


At least once a day I get yelled at or flipped the bird by an angry biker who doesn’t believe they should ever have to apply their brakes, or even move slightly in their lane, much less stop at a stop sign. Yesterday I saw a cyclist spit into the open window of a man who was parallel parking on a busy city street. There were 10 or 20 cars lined up behind the parallel parker, all of them civil. Driving in the city you kind of learn – sometimes you won’t be able to travel between two locations in an undeterred path at top velocity. This should be expected – even by bikers – I mean there are other people amuck in this GIGANTIC F*CKING CITY!


I am sorry. I shouldn’t have used caps-lock. A woman got fired for using caps-lock all the time in her email correspondence with colleagues. Seriously. Google it. I think it was in England. Anyway, let me know what’s up, and how I should deal with my aggression toward cyclists. As much as I’d like to, I don’t want to start running down bikers in the street. Jail is scary.


All the best.


Ten Thousand Points for a Biker


PS – None of this applies to those tall bikes. I love those tall bikes! How do they get on those?


Dear Ten Thousand Points for a Biker,
Don’t worry about the caps lock thing, you’re in a safe place here.


While I think you make some excellent points, we must be cautious not to condemn people based on their hobbies. I can’t get all caught up in whether or not people are going to be judgmental about my serial killer collages or my erotic cake baking. Just kidding, I don’t really bake erotic cakes.


Now, if we want to examine Bike Riders and their habits in the city we can do so respectfully. It is unknown whether Bike Riders are born that way, or if their transportation orientation is a choice. We’ll leave that argument to the scientists and the Christians. Our main concern as drivers is why they act like such tools. Maybe it’s an inferiority complex, maybe it’s jealousy that they don’t have a car, maybe their behavior springs from a smugness that their carbon footprint is smaller than a motorist’s.


Really though I think it’s a matter of perspective. Once a month I get down on my hands and knees and crawl around my apartment, just to see what it’s like for my dog. Life is completely different when you’re only two and a half feet at the shoulder. I’m pretty sure she’s always trying to get on the couch because she wants to see what life is like up at my level. I mean my height, not my intellectual level- she’s already surpassed me intellectually.


Bike Riders have a totally different view of the world: they’re not encased by metal, they don’t have windshields or places to stash their unpaid bills, or heated seats. It’s just them and the bike. And a lot of enemies in cars, mucking up their system. I don’t agree with the lifestyle, but I understand it.


Regarding those tall bikes, I too am pretty delighted and mystified by how they get up there. And what happens if they fall? It seems pretty precarious and a long way to the pavement. Maybe another reader could enlighten us?


Poor Lucky Me

List – Monday November 9th

3414946652_a670f810fbTen Indications That You Might Be A Total A-Hole Behind The Wheel*:


1. You text/email/check your facebook page/do your make up/read the paper (seriously, I’ve seen several people doing this) while driving.


2. You think it’s perfectly fine to budge the line of traffic at on off-ramp by riding the shoulder, then act pissed off when people don’t let you in.


3. You honk at the person in front of you as soon as the light turns green.


4. You have more than one religious, political, or “funny” bumper sticker on your car.


5. You use your brakes when merging.


6. You are a cab driver.


7. You never care whether or not you are within the yellow lines of a parking spot and that you may be screwing the guy next to you by parking so close to his car that he has to climb out the passenger side and resort to spitting on your car out of fury.


8. You have a pair of plastic testicles hanging from your truck hitch.


9. You smoke in your car and throw your cigarette butts out of the window.


10. You drive unnecessarily close to bikes and pedestrians just to “show them who’s boss”.


* If you identify with more than one of these traits, please seriously consider your motorist style.

Chore Wheel Spins Out Of Control – Friday November 6th

69464654_85618623cfDear Poor Lucky Me,


My roommate and I get along really well. We’ve lived together for 4 years and it’s worked so well because she does the dishes (which I hate) and I do the laundry (which she hates). The problem is lately I’ve started really REALLY hating the laundry.


Do you think it’s cheating if I send the laundry out? My dry cleaner does it for like $2 a pound and I’ll pay for it.


I guess I hate doing the dishes and doing the laundry.


I’m Beginning to Think I’m Lazy


Dear I.B.T.T.I.L.,
Maybe laziness doesn’t have to be measured by one’s enthusiasm for chores. My shower looks like a science experiment gone awry but I don’t think that makes me lazy. Cleaning sucks and isn’t satisfying because you have to do it so regularly.


What makes me lazy is when I drop the clicker behind the couch but don’t want to reach for it so I keep watching “How It’s Made: Baseball Gloves” for another 90 minutes. Or when I have soup for dinner and don’t microwave it long enough and just eat it cold instead of standing up and walking back into the kitchen with it. Or when I use a fine pointed sharpie to alter the date on my Jiffy Lube windshield sticker so my roommate thinks I’m taking the car to get regular oil changes. Actually that one falls into the laziness and deception category, and I hate liars, so maybe I’ll get the oil changed after all. Eventually.


The point is, you’ve come up with a win-win solution. You and your roommate have clean clothes, and you don’t have to do the laundry. I think it’s genius, well done.


Poor Lucky Me

Photo Day – Thursday November 5th




This is a photograph of a piece of art I wanted but was too cheap to buy. I think it is a famous piece of art. If I owned it I would put it above a grand fireplace in my library.


Sometimes you don’t want art that is all representative-y, you just want a portrait of a really cultured and wealthy dog.

Celebrity Look Alike Not Pleased- Wednesday November 4th

flockhart-calista-photo-calista-flockhart-6221378Dear Poor Lucky Me,
People keep mistaking me for the actress Calista Flockhart. I’m sure she’s a really great person, but I’m still pretty insulted.


Alley McBeal was a stupid show and Flockhart’s claim to fame (as far as I can remember) was being grossly skinny.


What can I say to people when they tell me I look like her, and how can I find out if I really DO look like her?


My Self Esteem is Taking a Beating


Dear My Self Esteem,
I don’t know, I mean looking like Calista Flockhart is better than Rachael Zoe or Paul Giamatti. People just say that kind of stuff because they don’t know how to make conversation they think that’s interesting.


Your come backs should vary between (depending on the situation):


“I AM Calista Flockhart”


“I actually had my face surgically altered to look like Calista Flockhart”


“No, Calista Flockhart looks like ME”


It’s important not to back down. Insist that you’re telling the truth until the person feels uncomfortable and changes the subject or asks for your autograph. If they don’t change the subject fast enough, look around frantically and say “I’m being followed by paparazzi!” then push them out of the way and rush out of the room.


You’ll find out if you really do look like her based on people’s reactions to the statements above. If you have to really work to get the person to believe you, then you don’t look like that much like Ally McBeal. You’ll probably just thin and quirky. There’s nothing wrong with that.


Poor Lucky Me

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