A Girl's Guide to Chicago

by Kelly Russell

  I walk into the office happy and ready to start a new week. “Hi guys! How was everyone’s weekend?”

  The guys are not used to having a girl in the office being bright-eyed and cheery on a Monday morning. They’re barely awake and I get half-sleepy looks as they glance up at me from their computers.

  “Morning Kell. How was your weekend?” James gives me a bright smile. At least someone else looks awake.

  “It was good. I went home to the ‘burbs for the weekend.”

  I am growing to like James. He is one of my favorites in the office. We have been chatting through Yahoo Messenger and I stop by his desk at least once a day to talk. He has a great sense of humor and always makes me laugh.

  “What did you do?” I asked.

  “Well, Friday night, my friends and I went to this place on Southport and Newport called SoPo.”

  “What’s that? I have no idea where that is?”

  It’s in the Southport neighborhood, right next to Lakeview. SoPo is kind of a divey bar. I love it because they have five-dollar martinis all night, and they play the best music. Lots of pop mixed with ’80s and hip-hop.”

  “Ooh! That sounds awesome!”

  “You know what? We should go again this Friday. I think you will love it! My friends are going again, and you should meet them. They are really fun.”

  “This Friday? Okay! Yeah, for sure! That would be so fun! Okay, I will let you get to work, and I will chat with you later. I should get to my desk and start my day.”

  I walk over to my desk with an extra bounce in my step. Yay! I had city weekend plans, and it was only Monday. This is a great start to my week.

  Mid-morning, I’m still in a good mood, so I decide to send Jillian, the “shy girl,” an instant message. I’ve spoken to her a few times, and I’m interested in getting to know her better. She doesn’t really talk to the other girls and, now that I think of it, she doesn’t really talk to anyone. She mostly has her headphones on all day. So, before I can think too much about it, I tap out a message.

  What are your plans for lunch today? I feel like we haven’t really gotten to know each other. If you’re not busy, do you want to go to lunch today?

  The messenger bubble pops up right away, and she’s typing back. That’s a good sign. She responds, Sure, 1 pm?

  Okay, sounds great, see you at lunch.

  A little after one o’clock, Jillian walks over to my desk.

  “Ready?”

  “Yep. Just going to grab my coat.”

  “Do you like sushi? There is a good lunch sushi spot at the Illinois Center.”

  “I had lunch with Vin over at the Illinois Center. That must be a popular place to go. Is the sushi really good there?”

  “Yep, it’s really good. I promise. Going across the street is better than paying thirty dollars for lunch at a restaurant every day.”

  I nod in agreement. We take the elevator down and walk across to the Illinois Center. I decide that I can always get a California roll. You can’t really mess those up.

  The Illinois Center is super crowded again. The sushi place is a simple set up. You just pick up pre-made sushi in containers. They offer a variety, and it looks delicious. I still grab the California roll just to be safe.

  We don’t say much while in line to pay for our sushi. We look for a table and notice two girls getting up, so we rush over before anyone else grabs the table. As they get up, we set our sushi down on the table. We thank the girls for the table and sit down.

  “So, how long have you worked at the agency?” I open my container and pull apart my chopsticks.

  Jillian looks up at the ceiling, seeming to do the math in her head. “Oh. Only about six months.”

  “Oh really? I assumed longer for some reason. How do you like it?”

  “It’s good. I was tired of doing freelance stuff. It’s tough not getting a regular paycheck each month.”

  “I can imagine, especially in the city.”

  “Yep.”

  I take a bite of my sushi, and it is really good. “So, how long have you been in Chicago for?”

  “I moved here about two years ago after I graduated from Notre Dame.”

  “Oh wow! That’s impressive.”

  “Thanks.” She blushes a little and looks down. “I got a scholarship.”

  “That’s great! Do you still freelance on stuff or work on any fun projects on the side?”

  “Well, the coolest one is writing for a Chicago fashion and lifestyle blog called Second City Style.”

  “Oh my gosh! That is so cool!”

  “Yeah, it is sometimes. I write about Chicago fashion and cover events in the city. So, it can be fun to go out, meet people, attend events for free, and get paid for it.”

  “For sure. That sounds really fun.”

  “Well, if you like that kind of stuff, you should come with me to an event sometime. I’ll let you know when there’s a good event coming up.”

  “I’ve always loved fashion, and I would love too. It sounds pretty amazing.”

  “Cool. I will definitely let you know. So, how’re your first few weeks going? Where did you use to work before this?”

  “It’s going pretty well. I’m really enjoying what I’m doing. I was a preschool teacher, so this is totally a different world for me. However, I like my job so much that I think I’m going to put my teaching career on hold for the moment and focus on working at the agency.”

  “Well, that’s great. I’m glad you like it so much.”

  “Yeah, me too.”

  We finish our sushi rolls and head back to the office. We chat a little more about what she does for the blog. It’s really cool to hear about all the events she’s attended and written about. I’m going to check out this blog when I get back to my desk. Since Jillian knows about the latest fashion trends, maybe she would know what shoes are cute and appropriate for the city. She might even want to help me out and go shopping with me.

  I take off my coat and sit down at my desk. I get right up again to see if Vin is around. I don’t see him at his desk. He must have gone to lunch. I quickly type in the name Second City Style into the Google search field. I click on the first website that comes up. The blog loads a few seconds later. It doesn’t look that fancy. It’s not as clean and chic like Vogue’s website, but I can see that the blog not only covers events all over the city, but they also cover the latest in fashion trends as they relate to Chicago. This is seriously cool! I wonder how hard it is to get a blog up and going. I mean, I now work for a digital marketing agency. I’m sure one of the guys might want to help me.

  After daydreaming for a while about the thought of having my own blog, I tell myself, okay, let’s take a step back. One thing at a time. Let’s figure out this whole city living thing first. However, I can’t help but chat back and forth with Jillian a few times throughout the afternoon asking questions about the events she has gone to. I look at my computer, and I can’t believe it’s almost five o’clock. The first day of the week has been great. As I leave the office that evening, I don’t even feel nervous walking down Lake Street toward the train.

  The week continues to fly by, and before I know it, it’s Friday. James and I made plans to go home, freshen up and change, and to meet up at SoPo around seven. I am looking forward to going out. I haven’t been out in the city since I moved here, and I especially have not gone to a fun bar to go dancing.

  I happen to be chatting with James at his desk about our plans for the evening when Vin walks over.

  “Where are you two going?”

  “We are going to SoPo at Southport and Newport in Lakeview.” James looks over at me and grins.

  “Oh. What’s that? A restaurant?”

  “No. It’s just a dive bar with great dance music and good drink specials.”

  For a moment, Vin seems somewhat sad. Maybe it’s because we didn’t invite him. But do you really hang out with your boss outside of work? I don’t think so. I don’t think anyone from here d
oes. It would be kind of weird.

  “Well, have fun guys. Sounds like a cool place.”

  We both watch as Vin walks away.

  “He’s been kind of down the last few days.”

  I look back to James. “Yeah, I think he’s going through some stuff. Do you think we should have invited him?”

  “Nah. We’ve never hung out outside of work before. But maybe next time?”

  “Yeah, maybe.”

  I glance toward Vin again, who is back at his computer. A part of me feels bad for him.

  “Okay.” I turn to face James again. “So, I’ll see you later!”

  “Yep! I’ll text you when I’m in my cab.”

  At five o’clock on the dot, I close down my computer for the weekend and head out. I walk over and say goodbye to the girls at the modeling agency.

  “Bye! Have fun! We will definitely do drinks next week.”

  “Sound good!” I wave to the three of them and push through the glass doors. As I’m walking down the hallway, I hear footsteps behind me. My heart begins to race. After being mugged, I really hate it when someone walks up from behind. I spin around, and it’s Vin. My heart instantly returns to normal.

  “Oh hi. So, I didn’t ask you. What are you up to this weekend? Doing anything fun?”

  “Not much. Just dinner tonight with the girlfriend and maybe the bars tomorrow night with the guys.”

  He didn't sound excited about any of this. I want to ask him what was wrong. But it just doesn’t seem right or the right place. He’s my boss after all, and we are not really friends.

  “Well, that sounds fun. I hope things are better now.”

  “It’s the same, but it’s okay.”

  We walk out to Michigan Avenue and stop on the sidewalk.

  “Okay. Well, have a good weekend. I’ll see you on Monday!”

  “Yeah, you too Kelly.”

  We part ways and walk in opposite directions.

  I get off the train and walk as fast as I can to my apartment. It was already five-thirty. I need to shower and get ready for my first night out. I run up the stairs and into my second-floor apartment. David walks out of his room.

  “Are you okay?” He’s looking at me strangely.

  “Yep! I’m great! Just wanted to get home quick and get ready for my night out.”

  “Oh. That’s right. The way you ran up the stairs, I thought something was wrong. I forgot. Dancing with James.” He changes his voice to sound dreamier.

  “Umm. Do you think I like him or something? Because we are just friends. I’m absolutely pretty sure he’s not into girls. He might be your type though?” I give him a playful look and smile. I totally wouldn’t mind if my brother and my new friend started dating.

  “Do you want to join us? You can definitely come. It will be fun!”

  “Nah I can’t. I’m getting up early to go home in the morning.”

  “Again?” I give him a sad face. “I was hoping that we could hang out together and do some city stuff.”

  “Sorry, I already made plans with friends at home.”

  I sigh and walk away. David has not spent one full weekend yet in the city. I need to sit down with him and see what was going on. We have only been here a few weeks so surely, he would want to be in the city on the weekends? Didn’t he want to get to know the city like I do? I promise to talk to him this week. However, now isn’t the time to start that long conversation. I have to jump in the shower and get ready for my night out.

  I look around at my rolling rack of clothes. I really need to freshen up my wardrobe. Everything seems so outdated. I decide to wear a pair of black jeans, a black top, and my black boots. You can’t go wrong with all black. Simple and casual.

  I’m ready by six forty-five. I make a final outfit and makeup checks while I wait by my phone. At 7:04, James sends me a text me and says he’s walking out to get a cab. I grab my coat, run into David’s room, give him a hug goodbye, and I walk as fast as I can down the stairs.

  Of course, it’s dark out on my street, but a few people are walking about outside. Ahead, I can see cars at the top of my street at Sheffield. I hurry to reach the main road and look out for a cab. Luckily, one stops a few minutes later, and I get in. The driver asks, “Where to?” I pull up the directions on my phone. “3418 N. Southport.” Two seconds later, I’m on my way.

  There are a lot of people walking into the bar as I pull up. Inside the bar is already busy. I pull out my license to show the guy at the door. He checks my I.D. and waves me in. I see James waving at me from the bar in front. His other hand is holding a red martini. As I walk over, the bartender puts another one down on the bar top.

  “Here you go!” James yells over the loud music and passes me the drink.

  “The first one's on me. I hope you like Cosmos.”

  “Thanks!” I yell back, grabbing the drink off the bar.

  I take my first sip. You can tell it is cheap liquor. Too many of these and tomorrow will be a rough morning. Then again, who cares, tomorrow is Saturday. I didn’t have any plans. It’s time to have some fun and make the most of my night out.

  We finish our first round of drinks rather quickly, and I order a second one for both of us. We get our drinks a few minutes later and head toward the side of the dance floor just as a Britney Spears remix came on.

  “This is so fun!”

  He nods in response. “Come on!” He grabs my free hand and we head toward where a bigger crowd is gathering on the dance floor.

  Five drinks and five hours later, we are still dancing. My feet are killing me, but this is the most fun I have had in a while. James’s friends are with us. They are a fun group of guys and so nice. I’m thrilled to be out and meeting new people.

  Around one in the morning, we all decide to call it a night. We grab our coats that are stacked up high on a nearby chair. We head outside to catch our cabs. I’m tipsy, but James gets me a cab before getting his own. I hug everyone, wish them goodnight, and head home. I give the driver my address as I lay back against the leather seat. This has been such a great night!

  Thirty minutes later I’m home, my makeup is off, and I’m in my bed. I text James and tell him how much fun I had. He responds right away saying we should all go again another Friday. I respond “yes” and put my phone down. I settle down into my bed, and I fall asleep right away.

  I’m slightly hungover the next morning. I knew I would be, but that’s okay. It’s to be expected after all those cheap, sugary drinks. I crawl out of bed. The wood floor is cold beneath my feet, and I wince. My feet are still sore from all the dancing.

  I walk out into the living room, and the apartment is quiet. David has left for the weekend. I don’t want to sit alone in my apartment all day. I grab my phone from the bedroom that is charging by my bed. I see a text from David saying he has left and will be home tomorrow evening. I sit on my bed and text him back. I scroll through my phone to find Jillian’s number that I stored a few days earlier.

  I sit and think for a few minutes as to what I’m going to say. Why am I so awkward? Just send her a casual text and ask her if she wants to meet up or something.

  Happy Saturday! What are you up to? If you are not busy, do you want to meet on Michigan Ave to shop for a bit?

  I put the phone down and walk to the bathroom to start getting ready for the day. A few minutes later, my phone beeps. I finish brushing my teeth and walk through the kitchen and living room and into my bedroom. There’s a message from Jillian.

  Sure! What time?

  I look at the time. It’s ten-thirty.

  How is around noon at Michigan and Chicago Ave?

  Jillian lives in the Gold Coast, and I can get off the train at the Red Line and walk over to meet her. In the kitchen, I fill a glass with cold water, take two Advil, then take a nice hot shower. I’m happy to have some plans so I won’t be sitting in the house all day. Having something to do will also help me push through my hangover. I slip on a navy-blue sweater, jeans, and head
back to the bathroom to do my makeup and straighten my hair.

  Forty minutes later, I’m ready to shop. I leave my apartment and start my short walk to the Brown Line. As I walk up the stairs to the platform, I remember that I can switch to the Red Line at Fullerton, which is the next stop on the Brown line. I’m starting to get this whole train thing. It feels good. I adjust my scarf and zip up my coat. Standing outside in the cold is the worst. I see down the track that the train is coming. A minute later the train arrives, and I get on and take the quick ride over to Fullerton. I get off the train just as the Red Line comes into the station. I quickly get onto the Red Line and take the ten-minute train ride downtown to the Chicago Avenue stop.

  It’s my first time getting off the train at Chicago Avenue, and I quickly realize that I’m in a busy part of the city. I pause to figure out where to go. People are pushing past me. There are four different exits, and I look around at each one. I have no idea which stairs to take. I pick what I think sounds right and slowly walk up the dirty train station stairs.

  At the top, I see a McDonald's sign. I move to the side of the sidewalk so I can figure out which direction to go. I turn around. I don’t see much west on Chicago Avenue, at least nothing that looks like the direction of Michigan Avenue. I turn back around and start walking toward what I think is the right direction. I reach the next street and see a street sign that says, Wabash. Yay! I did it! I’m so proud that I have taken the train all by myself to downtown, and I don’t even feel that nervous. I find myself smiling at that accomplishment.

  I reach the Park Hyatt hotel and decide that this is a good place to text Jillian. I let her know that I’m here. She responds a minute later with a “be right there.” I stand under the heat lamp to keep warm and watch the shoppers pass by. I hear my name and realize Jillian is standing next to me. I was watching two ladies walk by. Each was wearing beige wool coats and beautiful designer bags. Where do they get clothes like that? I notice that Jillian is also wearing an oversized leopard-print faux fur coat and tall flat black boots.

  “You in dreamland or something?”

  “Nope. Sorry!” I quickly snap back to reality. “You ready to go do some shopping? I really need a pair of better boots. Something that I can wear to walk around in that will also be okay for the snowy weather.”