Every Awkward Thing I've Ever Done

Housesitting Fail: Part II

My parents’ friend was going out of town for a week and needed someone to watch her awesome loft apartment in Chicago.  I was a Senior in High School and this was like a dream come true.

When I showed up for a tour of the apartment, with my mom, their friend showed me around.  The place was amazing.  It had a rooftop patio AND a separate balcony.  It had an exposed brick wall and a spiral metal staircase.  It looked like an apartment from a movie, somewhere an artsy and independent romantic comedy heroine would live.

"You have to promise no one else will stay over.  Your boyfriend, your friends, no one can stay here but you.  And of course, no parties," my parents’ friend said in front of my mom.  Then she led me out onto the balcony and whispered: "But if you do have a party, make sure people go out onto the rooftop deck to smoke."

What?!  Had she just basically told me to have a party?

It was her apartment, if she told me to have a party who was I to disagree?  In fact, just to do my job better, I had two parties on two consecutive nights.  My boyfriend was there for both and he stayed with me at the loft.  We pretended that we were real adults and that this was our apartment.  We stood on the balcony and surveyed the city, trying to act as though we looked out at this view everyday.

Pictures from the party (note the exposed brick wall and spiral staircase, it’s like you’re watching a Kate Hudson movie right?)(also I’m going to assume that was my “adult” shirt):

The next morning I woke to the screams of an Eastern European woman.

I was lying in bed, mostly naked.  The apartment was covered in empty beer cans.  The place was a mess.  

The Eastern European woman continued to scream.

I punched my boyfriend.  ”Do something!”

"Who are you?!  What are you doing here?!" the woman screamed.

My boyfriend struggled to find his jeans.

"We’re housesitting.  Didn’t she tell you?  I swear, we’re supposed to be here."

"No, she didn’t say anything.  Who are you? I’m calling the police!"

"Who are you?" I asked.

"I’m the cleaning woman.  I clean her apartment once a week.  She always tells me when someone will be here and she didn’t say anything."

"We’re housesitting!  She knows we’re here."

The woman looked around at the mess and shook her head.  ”No, no.  This isn’t right.  I’m not cleaning this up!”

"No, you don’t have to.  We’ll clean it up.  You just leave and we’ll clean it up."

"I’m telling her about this."

"No, please don’t.  We’ll clean it up!"

We finally convinced her to leave, and we spent the rest of our housesitting time cleaning.  It was like being a real adult.

Friday night.

Friday night.

TBT: Graduations

I recently found this amazing photo taken on the day of my 8th grade graduation:

My favorite part of this picture has nothing to do with me and everything to do with that sick pocket watch chain (I really hope it was a pocket watch chain, although the late 90s was also the time of the wallet chain).  

In my town, instead of graduation gowns the boys just wore suits and the girls wore white dresses.  To me, that makes sense for 8th graders, who, to be honest, don’t really need a graduation ceremony.  But it was also true for high school graduation, which ruined the teen movie graduation moment I had in my head.  We had no tassels to flip, or caps to toss in the air and then freeze frame on as the opening credits begin to roll.

Before high school graduation my friends and I spent weeks looking for the perfect white dresses.  I had no luck.  The day before graduation I still hadn’t found a dress, so I pulled my 8th grade graduation dress out of the closet.  I was six inches taller, but I still managed to wear the same white dress to my 8th Grade graduation and my High School graduation.  Luckily I had not grown breasts between the ages of 14-18 (and still haven’t to this day).

Oh, and yes that is terrifying barbed wire behind us in the first photo.  Our school’s football bleachers were under construction and so our graduation was held at a random football field in the Chicago ghetto.  As we waited to go out we had to stand in line in the tennis courts, which, instead of having nets, had waist high chain link fences to separate the two sides of the court.  Whoo-hoo for Chicago public schools!

Rooney wants a purse of his own.

Rooney wants a purse of his own.

Housesitting Fails: Part I

There was a call-in topic on the radio today about housesitting and it reminded me of the two times I housesat, both of which ended horribly.

Here’s the first:

When I was a kid I wanted to grow up to be a dog breeder (as I think I have mentioned).  Unfortunately my first (and only) attempt, at 13, was a bit of a failure as my dog only had two puppies.  We kept one and sold the other to the family who lived across the street.  When they went out of town a few months later they asked me to dogsit/housesit.

(C.C. and Sprite/Jack dressed up for Christmas/Chanukah)

I had named the puppy I sold them “Sprite” because I had an obsession with Coca-Cola products (my other dogs were named Coco for Coca-cola, and C.C. for Cherry Coke), but they had changed his name to Jack. They also had another dog that had some pretentious greek mythology name, but which they called THE MONSTER.

"Don’t worry about trying to walk The Monster.  She’s too crazy to walk on a leash.  She’ll pull you right off your feet.  You can just let her out in the backyard."

It turned out these people were HORRIBLE dog owners.  Poor Jack (I still think of him as Sprite) was locked in a cage all day and when I let him out he had so much energy he could barely control himself.  Meanwhile, The Monster was one of the sweetest, calmest dogs I had ever met.  She loved cuddling, and when I decided I would try to walk her on a leash after all she walked calmly right beside me and didn’t pull at all.  I couldn’t imagine what horrible things they did to make her act like a monster around them.

One day I brought my friend with me to watch the dogs and as I was freeing Sprite/Jack from his cage in the basement she walked behind the built-in bar and found… a hunting rifle.  We had never seen a gun in person before and we took turns holding it and posing like redneck Charlie’s Angels.  Luckily there were no bullets in it or this would have been a much bigger housesitting fail.


This gave us an idea… We should search the rest of the house!  

Other than the rifle we didn’t find much in the basement, or on the first floor, so we headed upstairs.  There were three, totally normal children’s bedrooms.  There were two totally normal bathrooms.  And then there was the parents’s bedroom.  At first glance everything looked normal in here too, then we found it: an entire dresser drawer full of porn DVDs.  AN ENTIRE DRAWER.  Do you even know how many porn DVDs fit into a dresser drawer?  The answer is more porn DVDs than you will ever need.  They must have single handedly kept the local sex shop in business.  


(Not their actual drawer.  The porn in their drawer was much racier… )

That’s when we heard the front door open.  We hurriedly crammed the porn back into the drawer, but we weren’t fast enough.  We stumbled out of the bedroom just as the childrens’ nanny reached the top of the stairs. 

"What were you doing in there?"

"I had a headache," I answered.  "I was looking for the aspirin."

"In their bedroom?"


"Not in the bathroom medicine cabinet where aspirin is usually found?"


"And it took two of you to look for the aspirin in their bedroom?"


When the family returned home I was given a stern talking to about having friends over without their permission and not respecting their privacy.  (That nanny was a total rat!)  I was never asked to dogsit again, and poor Jack/Sprite grew into a real monster, who growled viciously at anyone who walked by their house.  

There are two lessons to be learned from this experience:

1) Don’t sell a puppy to a family that refers to their other dog as The Monster.

2) Don’t ask a 13 year old to housesit if you have an entire drawer full of porn in your bedroom.


Overheard at Starbucks: The Correct Guess

6-year-old to his 4-year-old brother:  When I’m grown up, you’ll never guess what I’m going to  spend all my money on.

4-year-old brother:  Kitty cats?

6-year-old:  You guessed the correct guess.

My Moms Take On My Dating Life

A few weeks ago I posted something about my dad’s take on my dating history.  I recently learned something about my mom’s take…

When I left for college I was in a “serious” relationship.  We were planning to get married.  We had exchanged rings.  I mean, we had been dating a whole 9 months!  We were obviously life partners!

For the first semester I flew home once month and he came to NYC once a month.  But that wasn’t good enough.  By my second semester he had moved to New York, was working at a burger restaurant, and living in Alphabet City with three (really weird) strangers he’d met on Craigslist.

When the year, and my university housing contract, ended I told my mother that my boyfriend and I were going to get an apartment together.  I was 19, he was 22.  I expected her to tell me we were crazy.  We were too young.  I should stay in the dorms so I could make more friends and have a real college experience.  But she didn’t say any of that.  Her response was:  ”Okay, let’s call a realtor.”

A month before school started she went to New York with me and helped me find an apartment.  Then she came back with us when we moved in and helped decorate and pick out furniture.  I thought I had the coolest, most understanding mom in the whole world (and I do, but for completely different reasons than I thought then).

Four months later my boyfriend and I broke up.  My (ex-)boyfriend moved back to Chicago and a friend moved into the apartment with me.  (Those two later started dating behind my back, but that’s a story for another time…)

Recently, after a few glasses of wine, I asked my mom why she had let me move in with my boyfriend when I was obviously too young and immature.  Didn’t it scare her that we were talking about getting married?

"Of course I knew you shouldn’t marry him.  That’s WHY I let you move in together.  You were 19!  He was 22!  I knew if you had to live under the same roof you’d drive each other crazy.  And that’s exactly what happened."

"Whoa, that’s so… devious."

My mom gave me a sly wine-drunk smile.

I have the coolest, most understanding mom in the whole world.

#TBT: I Wanna Be A Supermodel

Some people may think my proudest educational moment would have been getting into the film program at New York University.  Those people would be wrong.  My proudest educational moment was being “hand-picked” to attend Barbizon Modeling and Acting Center.

For those of you who have never heard of Barbizon, it is a sham “school” that sends cute girls to the mall to find younger, more impressionable girls and say to them “Oh My God!  Has anyone ever told you that you could totally be a model?”  Then,  when they inevitably say “Do you really think so?” the older girls slip those poor schmucks a Barbizon form.  

I was one of those schmucks.  I was “discovered” at the mall and immediately begged my parents to spend hundreds of dollars so that I could learn how to be a model.  I took classes in runway walking, manners/audition behavior, and doing my own make-up.  It was like the 1990s version of an 1890s etiquette class.

Our final exam was our very own runway show at which numerous other Barbizon students (numerous is code for no one ever) had been discovered by modeling agents and were now successful working models who didn’t get out of bed for less than $10,000 a day (which is code for they never get out of bed because they are unemployed).

And thus I give you this week’s #TBT, brought to you by the fine people at Barbizon.

Tell me that I am not selling the shit out of the outfit.  What ten year old girl wouldn’t want to dress as a hip eighty year old business man?  Unfortunately, and much to my surprise, my Barbizon training did not land me a lucrative career as a super model.  It did however get me one job:  doing a runway show at the mall for my very favorite store, Limited Too.  I was paid in the form of a $50 gift certificate.  Basically, my point is, it was all worth it.

Me at the Limited Too runway show:

Plus I got to keep that vest.

Overheard at Starbucks: The Vampires Stole My Boot

As an unemployed writer I’m at Starbucks A LOT.  And one of my many talents (some may not consider this a talent, but I do) is eavesdropping.  I am an excellent eavesdropper.  By the end of dinner I can tell you the couple at the table next to ours’s entire life story.  Unfortunately I probably won’t have heard a word you said.  You win some, you lose some.  

The Starbucks I frequent is in Hollywood, and as anyone who lives in/has been to/watches TV knows, Hollywood is full of crazy people.  Like, escaped from the mental hospital crazy people.  There’s a lot to eavesdrop on.

So… without further… I present you with a new feature I like to call:  Overheard at Starbucks.


The window seats at this Starbucks are coveted because each one has it’s own electrical outlet and we are nothing if not a nation addicted to electronics.  My laptop battery was dying low and I was on the look-out, waiting for someone to leave so I could pounce.  I noticed a disheveled older man in one of the seats packing up his stuff.  I was about to pounce, but then I noticed something.  He had left one boot under the table.

Why would he do that?  Had he not realized he left it?  How do you not realize you left a boot behind?  Was it garbage he was too lazy to throw in the trash?  OR… was it a hobo sign that meant “my boot is here, so obviously I am saving this table and I will return for it later and if you try to take the table you will have a hobo curse cast upon you”?

I assumed the latter and left the table alone.  Another customer, less versed on hobo signs I guess, didn’t notice the boot, and took the table.  Nothing bad happened to him.  No hobo curse befell him (unless it was a slow acting curse and he wouldn’t show signs of it for days, or months, or even years; he might die at 80 of seemingly natural causes but it would really be the hobo curse in action).  I kicked myself for letting the table go.

Then, a half-an-hour later, the disheveled man returned.

"Sorry, my boot’s under there.  The vampires took it and they hid it from me.  They’re always meddling.  Meddling vampires.  They just won’t leave me alone."

The man at the table looked terrified.  He quickly handed over the boot.

So I guess I’m not as good at reading hobo signs as I thought.  That boot didn’t mean “this is my table, leave it alone” it meant “I’m a fucking wackadoodle nutjob and the vampires won’t leave me alone”.


TBT: Business on the Top and Party Nowhere

It was the day of the 8th grade winter dance.  I had always had long hair.  Super long hair.  Long, ratty, unbrushable, is-it-curly-or-is-it-a-rat’s-nest? hair.  So I decided to cut it all off.  I bought one of those hairstyle magazines and found the exact cut I wanted.  It was short, young, hip.  It was going to be the new me.  I would walk in to the dance and everyone would stop and stare.  The DJ would stop playing and the record would scratch.  It would be like a scene in a movie, where the nerd girl is suddenly transformed into the popular girl and everyone is amazed.

I brought the picture to the salon down the street.  The salon had a fancy sounding name, a man’s name made up of two first names.  John Thomas, Ryan Patrick, James Anthony.  (It’s the last one.)  But inside it looked like an Italian family’s living room.  All of the stylists were little old Italian women.

I gave one of the women my picture and she said something along the lines of “No problem” in a thick Italian accent.  I cried when a foot of my hair hit the ground, but I told myself it was for the best.  The transformation was coming.

Finally she told me she was finished and I turned to face the mirror.  I looked like an Italian mob wife.  There was a huge ratted poof on top and then it sort of flipped under in a 60’s style.  It was business on the top and party nowhere.  It looked horrible.  I started to cry again.  I didn’t even have time to try to fix it.  I had to get ready for the dance.

The dress I had bought for the dance was a black slip dress with a see through sheer lace dress that went over it.  With my young, hip haircut I thought it would look sophisticated.  With my new haircut it looked like I was dressed up as a grandmother for Halloween.

The first person who saw me was one of the cute boys in school.  His mouth dropped open and he started laughing.  I have never been so mortified.

Unfortunately I don’t have a picture from that dance.  Probably I wouldn’t allow my parents to document my humiliation.

When I washed all of the crunchy, goopy product out of my hair it looked a little better.  Over time I got better at styling it myself.  But it will probably always be my biggest hair cut mistake, as you can see in my yearbook photo.

I’m getting my hair cut tomorrow.  Wish me luck.