A Girl's Guide to Chicago Read online

  I looked down at my heeled boots. “These are just not great for walking around the city, and they’d be terrible in the snow.”

  “Oh, no, you can’t wear those! You will literally slip and slide all over the place.”

  “Okay, where do you think we should go? I’ll just follow you!”

  “Well, since we are close, let’s start at Macy’s. Then we can head down Michigan Avenue.”

  “Okay, sounds good to me!”

  I tell her about my fun night at SoPo with James. I suggest that we should all go sometime. “I’d love to go,” she says. But I know that with or without her, I’m definitely planning on going again.

  As I open the large door to Macy’s, a family of four pushes through from inside. The parents look miserable, and as they drag their kids out of the store. I give Jillian a look. We step to one side and happily let them through. The store is packed with shoppers. We stroll through the first floor and head up to the shoe department. It’s huge, but I don’t see much that I like. It’s near the end of boot season. I think it’s going to be difficult to find something.

  “Okay, let’s go. I’m not seeing anything I like here. Let’s just walk down Michigan and see what we can find.”

  A few minutes later we are back outside into the cold and heading down busy Michigan Avenue.

  “So, last night I attended an event for Second City Style. One of the boutiques in the Gold Coast was having an event.”

  “Really? That sounds fun! Did you go with friends?”

  “No, just me.”

  “Oh. Don’t you get nervous going alone?”

  “No, I’m used to it. I usually end up knowing someone anyways. It’s fun of course, and I like it, but I know the routine now. You go, have some champagne, engage in some small talk, take some photos, and you leave.”

  “Still. Just going to an event like that sounds really fun and like something you would see in the movies.”

  “Well, they are not always that glamorous. Like I said the other day, I promise, you will get to go sometime.”

  “Well, I can’t wait!”

  We pass a shoe store and decide to head inside. The store is full of gorgeous leather boots. I should be looking for something practical, but I instantly set my eyes on a pair of cognac knee-high boots. The color and style are just perfect. I know if I get a pair like these, I would have them for a long time. I pick up one boot and look at the bottom to see the price tag. They are $198, so I better really, really like them. I have never in my life thought about buying such an expensive pair of boots.

  Before I can change my mind, I ask the sales associate if they have my size and, of course, they do. I turn around and look at Jillian.

  “Well, let’s hope they look terrible.”

  Jillian gives me a look. We both know that couldn’t possibly be true. The sales associate brings the box over to me, and I try them on. It’s just what I was afraid of. These boots are gorgeous! The leather is soft, and they fit perfectly. They have a slight wedge, which is not ideal for walking around, but they feel more comfortable than my heeled boots. I should be shopping for flat, waterproof boots that are good for walking around the city. But, I love my heels and wedges. I’m apprehensive about making such a big purchase, since these boots are also a big chunk of my paycheck, but they are real city girl chic boots! I’ve seen so many girls walking around wearing boots like these, and I just have to have them.

  I take a few minutes to walk around and look at a few other pairs that are more practical. By comparison, they just seem so boring. The color and style of those other boots are so nice.

  “I should just get these plain black boots.”

  “Yeah, you can. But you could probably order a pair like that online for way less. Those cognac boots are really in right now. I actually just wrote a piece for the blog on stylish winter-to-spring boots and those boots are totally it. Plus, the wedge is not that high. You can definitely walk in them, just not miles.”

  “Okay. I’m sold. Now I feel like I need some nicer clothes, shoes, and accessories. Everyone walks around with these gorgeous coats, scarves, and boots, and I feel like my style is so basic and…”

  “Not a city style?”

  “Yes. I know it might sound silly, but I want to look good and to fit in.”

  “No. I get it. Style and fashion are a big part of the city, and you will find your style. Especially after you have been here for a few seasons.”

  “Okay. Let me go pay.”

  I grab the box and head to the counter. I also purchased the leather spray so I can make them somewhat waterproof. After tax and the leather spray, I leave the store with my brand-new city boots and $227.82 on my credit card.

  I promise myself that I won’t charge anything else. I will pay half now and half next month. This sounds like a good plan. I feel better already. I didn’t have practical boots, but I had the perfect “city girl” boots. If it snows again, I will just figure something out. I can also order a pair of black flat boots online, just as Jillian suggested and save these for when I’m going out.

  I’m happy with my purchase and my plan. We’re on Michigan Avenue again, and it’s cold, so we decide to warm up and grab a coffee and sandwich from Starbucks. Starbucks has pretty good sandwiches, and that would mean lunch would only cost me about ten dollars. After my expensive purchase, a cheap lunch sounds good to me.

  We pass the Ralph Lauren store on our way to Starbucks, and I notice the RL Restaurant that we passed earlier. It’s so charming with its big, wooden French-style doors and blue awning. It seems the perfect cozy spot on a frigid day. It’s a part of Ralph Lauren, and I figured it might be a pricey place for lunch.

  “What’s that RL place like?”

  “Oh, that’s a great place to go. You would really like it. Very cozy and tons of charm. They have good grilled cheese and tomato soup. Do you want to go there instead?”

  I do, and it sounds amazing. But I think it’s best to stick to the plan and just go to Starbucks.

  “No, it’s okay, we can save it for another day.”

  We cross Chicago Avenue, walk through the park past the historic Water Tower, then head left toward the Gold Coast. I love how quaint and beautiful this neighborhood is. We pass by Aritzia, Barneys, and Hermès. It’s so much fun to window shop. As we walk by, Jillian tells me there’s also a fabulous lunch spot in Barneys called Freds. She says they have the best salads and a quaint little outdoor patio in the summer. We head inside Starbucks, and we each order a hot drink; a white mocha for me, and a chai latte for Jillian, along with two sandwiches.

  We look for an open table while we wait for our drinks. This Starbucks has two levels, and it’s really cozy. We are lucky enough to find a table upstairs, close to the fireplace. We enjoy our sandwiches and drinks as we chat about work. We talk about how fun the other guys are in the office and how crazy some of our clients can be.

  “Speaking of crazy, what do you think about Mark? He’s always just parading around the office. But he doesn't seem to do much. He definitely doesn’t work as hard as the rest of us.”

  “I agree, he’s also not around much either. It’s very strange.”

  We switch the subject to the upcoming company outing, which we are both excited for if the team reaches our goal for February. We are ahead of schedule already, so everyone in the office is motivated to reach this month’s goal.

  We finish our lunch, and I look at my phone and see that it’s almost four. Jillian is going out with a guy that she sees regularly, but she says it's nothing really that serious. To me, she seems a little guarded, and I wonder what her story truly is?

  “Okay, well thanks for texting me, Kelly. It was fun to go shopping for shoes. I should head home to relax for a bit before I have to get ready.”

  “Yeah, let’s go. Thanks for going with me. It was fun.”

  We both stand up and throw our garbage away. I make sure I have my new purchase, and we head toward the door.

  “
Okay, Jillian. See you on Monday! Have fun tonight.”

  “Thanks, see ya.”

  I cross the street and head toward State Street. I make a left on State to head toward the Red Line station.

  It’s almost dark by the time I get off the train. It’s okay. There are plenty of people around heading out for Saturday night. I didn’t care either that I’m going home to an empty apartment. It has been a great weekend so far, and I didn’t feel as lonely as I did before. My attitude has definitely changed, and it is really paying off. I felt good about everything. I look forward to seeing how things will change even more for me over the next few months.

  I really do believe that if you want to make things better, you can. Sometimes, it is just about going after what you really want to do and having a positive attitude.

  I make some tea and popcorn, put on my pajamas, curl up on my couch, and turn on the TV to watch a sappy Hallmark movie. I just love these movies, they are such a good, guilty pleasure.

  Six

  I wake up Sunday morning just before nine with a text from my brother saying he’s heading back to the city in a few hours. His friend, Crystal, is going to drive him back, so he doesn’t have to take the train. He is going to her house first because she has something to show him. I decide to clean the house a little and get my laundry done.

  Around one in the afternoon, I hear two people walking up the stairs and figure it was my brother and Crystal. David bursts through the front door, his bag in tow with Crystal right behind him. I give him a big hug. I smile at Crystal and notice she is grinning and holding something tiny in her hands. It is a little black and white kitten and he or she is adorable!

  “Is that your kitten? It’s so cute! Why did you bring it here?”

  “Well, umm, my Dad was in the yard and noticed this tiny little thing. He walked over to it thinking it was a mouse or something and realized it was this kitten. He brought it inside because it was so cold outside. We couldn’t believe she had survived out there. We warmed her up and later that day, took her to the vet.

  The vet said she was fine and healthy, and we wondered where she had come from? We checked with a few neighbors around us, but they said they weren’t missing a kitten.

  I want to keep her, but our cat is so mean to her. She’s so tiny. I don’t want her scared or hurt. So, I asked David if I could bring her here to see if you would take her for a bit until I find someone who wants her. She’s so sweet, and David said it is up to you. So here she is.”

  Crystal hands me the tiny kitten, and I cradle her in my arms. She is such a sweet little thing, but I don’t want the responsibility of a cat right now.

  “Ugh, Crystal, I don’t know. I don’t want to take care of a kitten right now.”

  “It won’t be for long. I promise! I brought you all her things. You just might need some more food, litter, and a litter box.”

  I sit down on the couch, and the kitten immediately curls up in a little ball in my lap.

  “Okay, fine. Little kitty can stay for a few days. But, I don’t want a pet right now. So, you need to find her a home.”

  Crystal looks over at me and smiles. “Yay! Great! Thank you so much! Okay, well I should really start heading back home. I will keep you guys posted and try to find a home for her asap. Thank you, guys, so much for taking her.”

  “You’re welcome. It’s no problem.”

  “Well, Okay, I’ll see you guys soon.”

  Crystal gives us each a hug and heads out the door. I told her having the kitten is no problem, but I’m really not happy about this. I’ve never had a cat, and I have no idea what to do with one. David closes the door behind her and comes over to sit with me on the couch.

  “Kelly, I’m so sorry about this. I didn’t know what else to do. She kind of trapped me when she told me to come over this morning. She asked me if we could take her in front of her family, and I felt like I didn’t have a choice.”

  “It’s okay. We’ll figure it out. I think we should go to the store soon to get kitty whatever she needs. She might have to use the bathroom or something?”

  I just bought those expensive boots, so I’m already feeling guilty having to put more money on my credit card. Hopefully, the things we need to get for the kitten won’t cost too much. I decide now would also be the time to have a little chat with my brother. We put the kitty in a blanket on the dining room chair. She looks so cozy.

  “Well, David, she’s definitely a sweet little thing.”

  “She is, she looks like a little cow cat.”

  We throw on our coats and shoes and head out the front door. We walk toward the Petco on Halsted Street. I take a deep breath and think about how to start the conversation.

  “So, David, what’s going on with you lately? You don’t seem to like it here. You have made plans to go home every weekend.”

  He doesn’t say anything, so I continue.

  Also, what’s going on with the job situation? You know you need to get one soon. I can’t pay all the rent by myself. Why can’t you just get a serving job in the meantime?”

  “I don’t want to serve. I want to get a job as a personal trainer.”

  “I know. But, you could make good money and still look for what you want to do.”

  I can tell he’s starting to get annoyed. I don’t want to sound like I’m nagging, and I really don’t want this to turn into a fight. So, I change my tone.

  “Okay, listen. I’m sure you will find something soon. I have no doubt you will get the job you want. Keep being positive and maybe just look into some other options.”

  I feel a little annoyed that we can’t talk more about this. I am nervous that I’m going to have to pay next month’s rent. Spending the whole amount will really hurt my bank account and will make things financially difficult for me.

  We get what we need from Petco and walk back home. Things are quiet between us on the way back to our apartment. We head back up the stairs and walk inside only to find the little kitten still sitting in the blanket on the dining room chair.

  “Awe! How cute is she! She didn’t even move the whole time we were gone!”

  I set up a place for her food and litter box. I pick her up and show her where her food, water, and litter are. We spend the rest of the day hanging out with our new little guest. David doesn’t bring up our last conversation, and neither do I. The little kitten is a good distraction and breaks the ice after our talk. Hopefully, he will get a few interviews this week and figure it out.

  Later in the evening, as we are watching more episodes of The Office, the tiny kitten is curled up and cozy my lap.

  I look over at my brother. “So, should we call her Sophie or Gracie?”

  “I like Gracie.”

  “Yeah, me too. Sweet little Gracie.”

  Seven

  My alarm goes off. It’s Monday morning again. Don’t you feel like it’s always Friday and then before you know it, it’s Monday again? I feel that way. I didn’t sleep well last night. Little Gracie was climbing around and exploring my room most of the night. She is more active during the nighttime than during the day. However, I finally got her to settle down around two in the morning. I decided to let her snuggle in bed with me. She soon fell asleep next to me, and she seemed really content after that.

  Today, I’m wearing my new boots, because it’s a dreary day, and I need something to get me going. I’m on the train, feeling more tired than usual. I need to get my morning coffee from Starbucks. I look around the train. I think everyone feels the way I do. Tired.

  I’m downtown now, and fog is hanging low around the buildings. People are keeping their heads down as they make their way into their buildings. I guess this is what you would call the dead of winter.

  I walk into Starbucks and get into a long line. I have about ten minutes to be at work. The line is always so much longer on Monday mornings. I should know this by now.

  I give my order and try to be friendly as possible to the morning crew. I’m waiting
for my coffee at the end of the bar, and I hear my name called out. The other customers in line are not very friendly this morning, and I feel like someone has to be. I tell them all to have a good day.

  I push through the glass doors of the office and see that Vin is at his desk. He is early. He usually doesn’t come in until around nine-thirty. He looks up and motions for me to come back. Ugh! Not today. I want to get settled and drink some coffee. I put my stuff down and slowly walk toward his office.

  “Hi, Kelly. How was your weekend?”

  I have been in such a funk this morning that I forgot that I did have a great weekend.

  “Oh, we had a fun time at SoPo. We should all go sometime.”

  “Yeah. Maybe.”

  “How was yours?”

  “It was fine. So anyway. I got here early this morning to go over all our projects for this month. We are way ahead of schedule, and I think we will meet our goal.”

  “That is great.”

  “So, with that said, as one of your responsibilities, I would like you to come up with some ideas for the company outing.”

  “Okay. I can do that.”

  “Great. I will speak to James, so he can get things organized on his side. I will give you a budget, and you can start planning something for all of us. It can be during work hours as well. We can all take a half day, maybe on the last day of the month, which I think is a Friday.”

  “Perfect! I will start looking at some ideas.”

  I walk out of his office and annoy the guys by saying my morning hellos to everyone. No one seems to be in a good mood today, so I walk back to my desk.

  I spend the morning working on the new project that James has given me. I take a short break to instant message James and Jillian, so I can tell them about my brother bringing the cat home. They both think it’s crazy that Crystal would bring a cat over and ask me to take it. They ask if I’m going to keep her? I tell them I that I didn't want a cat at all, but she is so sweet. I don’t think I could give her up now. I have instantly grown attached to her. I have been wondering most of the day how she is doing.