A Girl's Guide to Chicago

by Kelly Russell

  We ride the train southbound, all the way downtown and around The Loop to the State and Lake stop. We get off and walk toward my new office. I feel so much better and much, much more confident knowing where I will be going in the morning.

  “Your new office looks like it’s in a really cool spot.”

  “Yeah, I think so too. I really appreciate you coming with me and helping me plan out my route. It definitely helps me feel less nervous about tomorrow.”

  “You’re welcome. I don’t mind at all. It’s nice to get out and explore the city a bit.”

  I look at David with a big smile. “I totally agree. Come on. Let’s go get some lunch.”

  We continue walking north up Michigan Avenue, and we end up at the Grand Lux Cafe. I have eaten here many times over the years, so it is easy and familiar. After our lunch, we walk off our meals and browse around the stores It is late January and getting dark and cold. And my feet! They’re killing me!

  I made the bad decision to wear my pointed-toe boots with heels that I always wear‒not a good choice for walking around the city. What type of shoes do other girls wear to look cute and still be able to walk around? I am definitely not used to doing this much walking. Maybe I just have to get used to it? Yes, I decide this is the case and try to ignore the pain in my feet. I will just focus on enjoying the rest of the day, but all I really want to do is hop in a cab and head home.

  So, I am wincing with every step in my pointed-toe boots, and I look over at David. He is happy as a clam‒in his tennis shoes. Ugh, guys! It is so easy for them.

  “David, do your feet hurt?”

  “No. Why?”

  “My feet are killing me! I don’t think I can walk around much more.”

  He looks down at my boots and laughs. “Why are you wearing those heels?”

  “They are not big heels, just kitten heels and these boots are usually fine. Just not when I’m doing all this walking.”

  “That’s ridiculous. You need tennis shoes or something.”

  “I know, but they don’t look as cute with my outfit.

  “You are so silly, no one cares.

  “Well, I do.”

  “Okay, well, it’s getting cold anyway, let’s head back to the train.”

  “Okay, good! Let’s go”

  Just when I feel like I cannot walk another step, we are on the train and headed home. This time we take the Red Line, then switch at the Fullerton station to get on the Brown Line, go one stop to the Diversey station, and we are home! It is so confusing, but I am just happy to be sitting down. City living is exhausting!

  I wake up on Monday morning, and I am nervous. I am panicking a little, my body is moving a little too slow, and I feel a little light-headed.

  “David?” He is still in bed. “Can you please come with me on the train again this morning? I don’t think I remember where I’m going. I just feel so nervous to go on the train alone.”

  What has had happened to me? I was fine this weekend. Quit being so nervous, I tell myself. I know where to go. I am supposed to be this cool new city girl who can do anything.

  I am being a huge pain, I know, but thankfully David is okay going with me. Maybe he is still feeling guilty about the bedroom?

  I try to calm my nerves. I take slow breaths. I face the mirror and finish straightening my hair and perfecting my makeup. I decide on a black skirt and a blue blouse that goes nicely with my blonde hair. Professional but not over the top.

  “Wow, you look nice,” says David, as I make my grand exit from the bathroom. I respond with a weak smile.

  “Kelly, you will be fine. Everyone is nervous on their first day. By the end of the week, this will all be easy for you.”

  “Thanks, I really hope so.”

  We do exactly the same thing we did yesterday. David is with me on the train all the way downtown and walks with me to the Starbuck below my office. I order a white mocha with no whip. I do love my morning coffee, but I also think drinking coffee is just what you do when you work in an office. At least, that is what people always did in the movies, and I just really want to fit in. I grab my coffee, and we head back outside.

  “Okay, good luck! Let me know how it goes.”

  “Okay, thanks! I will! Thank you also for coming with me.”

  “Of course, I get it.”

  I give my brother a wave and walk through the doors of my building. My coffee held confidently in hand, I walk into the office. Already everyone is busy at work on their computers. A guy with tufts of bright red hair poking out of a torn-up baseball cap walks toward me and points to a desk.

  “You must be the new receptionist. You can have a seat, and I’m sure James will be with you shortly.”

  “Okay, thank you.” My voice is almost a whisper. I give him a smile and try not look nervous. I sit down in my chair at my new desk.

  I look around at my new office. Big glass doors greet people at the front entrance that is just a few feet from my desk. The team is spread out behind me in a very large open layout. Most of the desks are all filled with my new co-workers who are busy tap, tap, tapping on their computers. There are no cubicles, only large desks grouped together by twos or threes. Each person has multiple monitors. The entire office is minimal, mostly black and white. The only color is the company’s logo on the sign behind my desk. The conference room and at least four offices are at the back of the office.

  The glass doors open, and three really pretty girls walk in and head into another big open room to my left. They are chatting with each other and do not notice me. I wonder what their jobs are here?

  Everyone is dressed so casually in their jeans, t-shirts, and ’80s-style knit sweaters. I look down at my black skirt, blue blouse, tights, and heels. I am beginning to feel very out of place. James did not mention anything in his email about a dress code. I tell myself it doesn’t matter, and I want to dress to impress. Of course, a casual sweater and jeans would not have been an appropriate choice for my first day.

  I poke around my desk to see if there are any clues as to what I was expected to do, but after a few minutes, James comes over.

  “Hi, Kelly! Let me show you around the office, and then we can get started.”

  “Okay. Sounds good!”

  I follow him around, and he introduces me to an office mostly full of hippie-type guys and one girl with frizzy, dirty blonde hair and big blue eyes. She seems really shy. James walks me past her desk, but she barely looks up at me.

  I am feeling shy too. I often get this way when I don’t know anyone. I hardly say a word during my introductions to everyone.

  My coworkers seem nice and very welcoming. I feel happy and somewhat at ease now. I was nervous. I feared that the office would be full of mean girls. I know, I am probably strange. But that is what I really thought. I obviously watch way too many movies.

  James spends about an hour explaining my duties to me. My main responsibilities are answering the phones, scheduling meetings, and setting up the conference room for meetings, and cleaning it up afterward. I am very nervous about answering the phone. I am a little overwhelmed. Everything about this position is all so new to me.

  “You look really worried. Do you have any questions?”

  “No. I’m just a little nervous. It just seems like there is a lot to remember.”

  “I get it. But you will be fine. I promise you will pick everything up really quickly. There is no pressure to learn everything today.”

  I sigh a little. “Okay. Yeah. You are right.”

  “Give yourself a break. It’s your first day.”

  “Okay, I will. Thank you for your help, James.”

  “Of course. We are going to be a team.” He looks down at his watch. “I have to get my day started and check on some clients. So, why don’t you settle in and I will check on you in a bit.

  “Okay, Sounds good.”

  James was right. I need to give myself a break. This is my first day at a new job with new responsibilities and in a diff
erent environment.

  “Oh, Kelly. One more thing. Vin will come over around noon and take you out for lunch.”

  I nod my head, smile, and walk back to my desk. I think to myself, oh great! I cannot wait. I wonder how Vin will be this time?

  It is one thirty. Vin hasn’t come over yet, and a few of the guys and the “shy girl” are headed out to lunch.

  “Hey, you want to come with us?” It is the guy in the torn-up baseball cap.

  “I’m supposed to go to lunch with Vin.”

  A guy with a huge head of dark curls chimes in, “Oh, he probably forgot. He won’t care if you come with us. We’re just going across the street to the deli and get sandwiches. We will be back in a few minutes.”

  I am rather hungry, and I want to get to know my new co-workers. After all, Vin was busy the first time I met him, so he probably did forget, and this little group is so sweet to have invited me to lunch. I feel a little relieved he hasn’t come over. I am not sure if my second encounter with Vin would be any better.

  “Okay. I’ll come with you guys.”

  “Okay great, let’s go.”

  I grab my coat and follow along to the deli.

  I am back at my desk, and just as I start to take a bite of my sandwich, Vin comes over to apologize for missing lunch.

  “I’m so sorry. It’s been a busy morning, but let’s go over some things this afternoon. Just stop by my office when you’ve finished your lunch.”

  Vin seems a little nicer today. I eat my lunch quickly. I do not want to keep Vin waiting too long. As soon as I am done, I brush the crumbs off my skirt, grab my mirror out of my purse and check for any leftover food or in my teeth. I quickly add some lip gloss and head to Vin’s office.

  I tap on his door lightly. “Come in,” he says. I enter his office and see his dark, long arms relaxing around his head. He leans back in his chair.

  “Hey! How’s the first day?”

  “Good so far. Lots to learn but I hope to learn everything quickly.”

  “That’s good. I’m not worried. I’m sure you will.”

  We spend the rest of the afternoon going over more of my duties. He asks me what other things I would be interested in doing around the office.

  “How do you feel about managing our schedules and doing a few things to help support the team?”

  “I can do whatever you need me to do to help.”

  “Good. Well let’s wrap up for the day and tomorrow I won’t forget to take you to lunch. I always like to get to know my new employees.”

  I shut down my computer and leave the office for the day. My first day was actually pretty good. It has been somewhat seamless, and I have to say that I really enjoy this whole agency thing. I am standing outside on the sidewalk of busy Michigan Avenue. I stand there, taking a second to remember which way to go. Hopefully, I can remember how to get back home.

  Three

  It is Tuesday morning, and I walk into the office for my second day of work. I sit down at my desk and look around. Just like yesterday, most of the team is at their desks working. I wonder what time they get here in the mornings? I turn on my computer and enjoy a few sips of my coffee. I look up as a guy in a white shirt, tie, a vest, designer jeans, and dark, thick, perfect hair comes charging through the glass office doors carrying a black Prada work bag. He looks like he just came straight from a modeling shoot. He stops at my desk, takes off his sunglasses, and looks at me.

  “Where is my latte and coffee cake? Each day, I would like my coffee and coffee cake on the edge of your desk, so when I walk into the office, I can just grab it.”

  I look shockingly up at the guy who is now staring right back at me. Who the heck is this guy? Did I miss something? Yesterday, when Vin told me I would be assisting the team, he did not mention anything about him. The guy in the vest and designer jeans continues.

  “Head down to Starbucks and get me a latte and a coffee cake.”

  I am so appalled that I just nod my head, stand up, and walk out the front glass doors. I walk out onto Michigan Avenue and back into Starbucks. I give the order to the barista.

  The Starbucks barista looks at me and starts chuckling. “Oh, honey! This order must be for Mark!”

  “Who? Oh . . . yes. I guess so.”

  The barista gives me a big smile. “Honey, oh my gosh! Mark is really something else. Guess I will be seeing you a lot more often then. I’m Frank.”

  “Kelly. Nice to meet you.”

  “You too, honey. Don’t you worry. I’ll get you that latte ASAP.” He hands me the coffee cake, and I walk to the end of the bar to wait for the latte.

  A few minutes later, I am back in the office with the latte and coffee cake in hand.

  “James,” I whisper his name as quietly as I can.

  “Where is the office of the guy who just walked in? I think his name is Mark?”

  James looks up from his desk and points to an office with the door closed. He gives me a smirk. “Good luck.”

  I walk over to the office and lightly knocked on the door. A voice says, “Come in.” I open the door. Mark is sitting behind a giant dark wood desk with a glass top. The whole office is designed to look like something out of Mad Men, complete with a bar cart. The entire office is dark. Dark gray walls and dark wood floors. The complete opposite of the rest of the office.

  “You can just put my latte and coffee cake there.” He points to the edge of his oversized desk.

  “You must be the new receptionist.” I nod and quietly respond “Yes.” I turn around and walk out, pulling the door closed behind me.

  As I turn back around, I bump right into Vin as he is walking toward his office. “Oh, I’m so sorry!” I almost knock his coffee out of his hand.

  “That’s okay. Good morning.”

  “Hmm Vin, can I ask you a quick question? Who is that guy in there?” I follow him into his office. “You didn’t mention anything about him yesterday.”

  “Oh, that’s Mark. He’s my partner for the modeling agency in the room right next to your desk. We all share this space.”

  “Modeling agency?”

  Yeah, I’m also part owner of a promotional modeling agency.” He points behind me to the room where the three pretty girls walked into yesterday. “The girls over there hire models to help with promotional events for our marketing clients around the city.”

  “Oh, interesting. Well, I just had no idea who he was. He came charging in and asked me to run out to Starbucks to get his morning order.”

  “Sorry, about that. He’s from New York City, and he thinks that’s the way it goes around here. Very Devil Wears Prada if you have ever seen that movie.” I smile back at Vin. Of course, I know that movie, but I am more surprised that he knows that movie.

  “I think he has the idea that your job is to personally assist him, even though I have told him that is not necessarily the case. He tried that a lot with our last receptionist.”

  “It’s okay. I just don’t want to pay for his Starbucks order every day.”

  “Oh. No. Of course not. Take some money out of petty cash. It’s in your desk. I will talk to him about you getting his Starbucks. We can figure out together what you can and can’t assist him with.”

  “Okay. Thanks. I just don’t want to cause a huge or awkward problem.”

  “No problem.” He sits down at his desk and opens his laptop.

  The rest of the day is pretty much normal. I am just trying to learn and remember everything I am asked to do. After each meeting, I head to the conference room to clean up and set up for the next. I try to be as confident as I can whenever I answer the phone. It is my least favorite part of the job so far. I think I sound so stupid, and I do not always know what to say.

  Today seems like a busy day. Everyone is buzzing around the office from meeting to meeting. I love this agency life, although it’s so different from what I’m used to, it’s exciting.

  Mark comes over to my desk late morning. I look up at him, ready for whatev
er he is going to ask me to do next.

  “Hey. Kelly, right?”

  “That’s me. Can I get something for you?”

  “No. No. I’m sorry for this morning. I think we got off to a wrong start. I’m Mark.” He puts out his hand. I stand up from my desk, so I can better shake his hand.

  “Nice to officially meet you, Mark,” I reply, sounding as professional as I can.

  “If I’m running late, would you mind getting my Starbucks in the mornings? I’ll give you my card when I come in. You’ll know what to get. A grande latte and a piece of coffee cake.”

  “Okay. I can do that. No problem.”

  “Thanks, Kell. That would be so helpful.”

  Vin must have talked to him. I was so grateful for that. Maybe Vin wasn’t so bad after all?

  Just before lunch, Vin introduces me to the girls from the modeling agency. Amy, Natalie, and Kourtney. Amy has long brown hair. She is cute and sweet, and she has a causal style like mine. Kourtney is tall. She has light brown skin, silky brown hair, and a perfect body to match. I notice her style is amazing and her clothes fit her perfectly. Natalie is short and somewhat boxy with long hair down to her waist. She keeps her style and makeup very simple. She is naturally pretty.

  These girls are really nice. Kourtney and Amy ask me a few questions to get to know me. As I am responding, I notice that Natalie is not listening. She is flirting with Vin, and he doesn’t seem to mind. Maybe they have a thing? I look back to Amy and Kourtney. They each give me a look that expresses exactly what I am thinking.

  “So. Kelly. We should go out for drinks next week or something after work?”

  “I would love that. Sounds fun.”

  “Okay. We will figure out which day works for all of us and let you know,” says Kourtney, but she is still watching Natalie.

  “Great. I’m pretty much open. Just still getting settled. Anyway, it was nice to meet you all.” I give one last look at Natalie who continues to chat away with Vin. I head back to my desk.

  Vin comes to my desk around lunchtime and asks me if I want to get some lunch.

  “There’s a really great soup place at the Illinois Center across the street.”