A Girl's Guide to Chicago

by Kelly Russell

  “Okay, if you really want to. I will cancel our table. I’ll be right back.”

  “Okay great! Thanks!”

  He gets up and heads over to the host stand. We will probably have to wait at least another twenty minutes for our table. I know I'm a terrible person but the vibe between us is so uncomfortable. He comes back, and we order some tapas. We sip on our sangria and wait for our food. There is a lot of awkward silence, and we mostly talk about what’s going on around us.

  We don’t have to wait too long for our food. This date is not going well, but the food is delicious. I love the Brussels sprouts salad. I need to come here again. I’ll have to ask the girls if they want to do a girl’s night here. Maybe next week. They have a happy hour. I snap myself back to reality and try to focus on our conversation. Am I the only person on the planet who has ever done something like this because I just feel so awful. I can’t get into this dinner, and my mind again continues to wander.

  “Hey, is everything is okay?”

  “Oh. Yeah. I’m fine. Sorry, I’m suddenly feeling a little tired. Must have been the sangria.”

  “Would you like anything else?”

  “No. I mean, no thanks, I’m full. Everything was so tasty though.” I give him a reassuring smile.

  “Okay, me too. So, where to next? What time are your other plans tonight? Not ’til later right?”

  I look at him and just stare. What? Oh no! Other plans? I completely forgot I told him that. I glance at my phone, and I see that it’s only 7:43 pm. We haven’t even been here for an hour. Oh geez! This guy came all the way here, and I’m only going to spend less than an hour with him. Of course, he wants to go somewhere else.

  “Hmm. I’m not sure. I’m going to go to the bathroom really quick. I will be right back.”

  “Okay. I will be right here.”

  I don’t know what to do. How am I going to get out of this? I look at my text messages, and I see a response from Vin.

  How’s it going?

  We are done eating, and he now wants to go somewhere else.

  You are done eating already?

  Yep. We ate at the bar. The conversation is really awkward. I don’t want to go somewhere else, but it’s only been 45 minutes.

  Just tell him you don’t feel well. I’m leaving right now to come get you. Be there in 10.

  Really?

  Yep.

  Okay.

  I can’t believe Vin is coming to get me. For a second, it makes me feel good, and I relax a bit. But, then, I feel nervous again. What am I going to tell him? How am I going to get out of here that quickly? I have never done anything like this before, and now I’m nervous. I never wanted to purposely hurt someone’s feelings. This is definitely a lesson learned, and I will never do anything like this to someone again. I walk back to the bar and hop back onto my bar stool.

  “So. What should we do? What do you like to do in the city?”

  “I’m so sorry. I think something didn’t sit well with me. I’m going to have to go home.”

  His face drops. “Really? Well, we could go back to your place and just relax.”

  “Oh, I don’t think that’s a good idea. I’m feeling worse every minute. I’m going to have to cancel my other plans as well.”

  “Oh, okay.” He looks really hurt, and I feel terrible.

  “Here. Let me get this.” I signal for the bar tab. “It’s my treat. I feel terrible, especially since you came all the way here.”

  He shrugs his shoulders as I hand my credit card to the bartender. I can tell he is upset, especially since he didn’t object to me paying for our meal. I deserve to pay since I was so misleading to this poor guy. I sign the check, and we get up to leave. A couple asks if they can have our stools, and I tell them yes. The fact that they seem happy to be out with each other makes me feel even more guilty. We walk out of the restaurant, and he sees a bar all lit up across the street.

  “I think I will just go over there.”

  “Okay. I’m so sorry.”

  He nods at me, turns away, and starts walking in the direction of the bar. I hear my phone beep, and I see a text from Vin that he is here. I watch until “Chocolate Chip Cookie Guy” is out of sight, and I look around for Vin’s BMW. I see him parked a few buildings down to my left. As I walk closer, he gets out of the car.

  “Wow! That was the quickest dinner ever! I was barely home before you text me back.”

  “What are you doing? Why are you getting out of the car?”

  “I’m letting you drive.”

  “What? No. I can’t! You said no before.”

  “Well, I trust you.”

  “Really?”

  “Really.”

  I give Vin a big smile and walk quickly to the driver’s side and get in. I buckle my seatbelt and grab the steering wheel. Vin gets comfortable in the passenger seat.

  I look over at him. “So, where should we go?”

  “Wherever you want. Just drive and tell me about your worst date ever.”

  “It was not a date. But, okay.” I pull out onto Halsted and head toward downtown.

  We spend the next hour driving around the city. I tell him about my dinner, and then we just talk about anything. Music, movies, places we want to visit. Talking with Vin is easy, unlike my dinner conversation this evening, and we laugh a lot together. Why can’t the guys I meet be more like Vin?

  A little later, we are driving down Lake Shore Drive toward my house. I ask him what he thinks of Natalie. I don’t know why I ask him. The question came out of nowhere, and I say it before I can stop myself. But, honestly, I am really curious.

  “Okay, where did that question come from? She’s nice. But we are just friends. She has asked me to hang out a few times.”

  “Are you going to hang out with her?”

  “I don’t know. We keep meaning to, but I haven’t really thought much about it.”

  “Oh, okay. I was just wondering.”

  He looks over at me and gives me a strange look. He starts to say something, but I cut him off and quickly change the conversation.

  “So, are you still coming to brunch tomorrow?”

  “Yeah, if you guys are still going.”

  “We are. I think we are going around eleven.”

  “Cool. I’ll be there.”

  “Okay. Hey, thanks so much for driving me, picking me up, and letting me drive your car. It was fun. I should be heading home. It’s still early, but I was out last night at Mercadito and had a few margaritas. I’ve been feeling tired all day. Have you been there? The drinks are great.”

  “Yeah, I’ve been there. Those drinks are pretty strong.”

  “Yeah, they sure are and, you know, every time I go out with James it becomes a long night.”

  A few minutes later we pull onto my street, and I park the car in front of my apartment. I take off my seatbelt and turn to look at Vin.

  “So, thanks again for everything tonight. It was fun, and I’ll see you tomorrow?”

  “Yep, of course. No problem. I’ll see you tomorrow.”

  I get out of the car and walk down the path to my front door. I turn around and watch him drive away. I let out a sigh. He did save me tonight. He’s really becoming a good friend. Other than James, I don’t know who else I would have called to help me out. I walk into my apartment and see that David is in his bedroom.

  “Hey, you’re home early.”

  “Yeah. I’m tired, and I didn’t want to hang out with that guy.”

  “That terrible? Two dates in a row.”

  “It wasn’t really a date, but yeah. It was just awkward. I told you about “Chocolate Chip Cookie Guy.”

  “Yep. You get yourself into some weird situations.”

  “Well, Vin picked me up early from my date, and we drove around for a bit. He let me drive his new car.”

  “Your boss picked you up and let you drive around in his car? That’s weird.”

  “It’s not like that. We are all friends in the office
. He’s also coming tomorrow to brunch. I’m excited for you to meet him and James. Jillian can’t make it, because she already has brunch plans. But you can meet her another time.”

  “Well, it’s still weird, but I’m looking forward to doing something tomorrow. I heard Ann Sather is good.”

  “I know! You haven’t really done anything here, you just work so much or go home. I really think you will like my friends.”

  “I’m sure I will.”

  Well, I’m going to get in my pajamas. Let’s watch some of The Office and catch up for a bit. The “Dinner Party” episode the other night was so funny. It’s probably one of my favorites.”

  “Okay. Yeah, it was too funny.”

  Thirteen

  David and I leave just before eleven to walk to Ann Sather for brunch. It’s finally a beautiful, sunny day, and it will be a pretty walk to the restaurant. The fresh air will feel good. Ann Sather is not far, just up Sheffield to Belmont, and the restaurant is about a block down on the right.

  “It’s so nice to be outside and not be freezing cold. I’m looking forward to walking around the next few months and finally have the chance to explore more of the city.”

  “Yeah, it’s nice. I actually walked all the way home from downtown the other day.”

  “Wow! You did? All the way from the Palmer House? That seems so far.”

  “It’s a few miles, but it’s a nice walk through Downtown, the Gold Coast, and Lincoln Park.”

  “How is work by the way?”

  “It’s good. I like it.”

  “What about the city? You don’t seem to do much here other than work. You go home most weekends.”

  “I just don’t really know anyone. I work weird hours, and I don’t have time to do much else. I will probably stay for the rest of the year and see what happens after that.”

  My chest tightens up as he tells me this, but I know that it’s true. He doesn’t seem that happy here. He’s not going out or doing anything fun. That’s why I want him to come with me today. I want him to meet my friends and have some fun.

  I can’t worry about next January. It is months away and maybe he will love working at the health club and will want to stay. Who knows what I will be doing, and where I will be with my job in January. I know can’t live with my brother forever, but I can’t afford to live by myself right now, and I’m not moving home. I’m starting to love my life in the city way too much. As we walk into Ann Sather, I smell the freshly baked cinnamon rolls, and my mouth starts to water.

  “Yum! Those rolls smell so good.”

  “Yeah they do, and this seems to be a popular place.”

  We arrive at Ann Sather, and it is super crowded. We squirm our way through the waiting customers and up to the counter. The hostess looks frazzled, but I ask her anyway if a James is waiting for us here. She doesn’t say anything, grabs two menus, and motions for us to follow her. We walk into a second room and James is at a table in the middle of the restaurant.

  “Hey, guys! I got here a little earlier to grab us a spot. It gets really busy here.”

  “I see that. James, this is my brother David. David, this is James.”

  The two shake hands and say hello. A guy comes over right away with glasses of water and asks if we want coffee. My brother and I say yes and within a minute we each have a mug in front of us filled with steaming hot coffee.

  “Okay guys let me tell you about Ann Sather since you haven’t been here before. You can order almost anything on the menu, and it comes with two sides. Everyone orders the cinnamon rolls and the potatoes as their sides.”

  I look at the tables around us. The portions are enormous, and the cinnamon rolls look like they could be a meal by themselves. It all looks so good. Vin joins us a few minutes later, and within a minute he also has a mug of hot coffee. James quickly again explains the menu to Vin.

  “So, Kelly. I’m not sure if you’ve noticed this, but brunch is kind of a thing that everyone does in the city.”

  “This is actually my first brunch experience in the city.”

  “Really? Okay, well good. This will be a good one.”

  We each tell our server how we want our eggs cooked. I ask for over-easy and go with James’ suggestion of the cinnamon rolls and potatoes. Minutes later, the server carries a large tray to our table with four enormous cinnamon rolls the size of my hand.

  “Wait! We each get one of those?”

  “Yep!”

  Each order comes with two rolls spackled in thick icing. They smell ridiculously good. The same server fills our coffee mugs, and we dig in. I take a deep bite into the roll as the warm gooey icing dribbles onto my chin. Oh my gosh! It’s heavenly. I end up eating most of the cinnamon rolls, and I can’t believe I have more food coming. I definitely can’t eat like this all the time.

  Our food arrives, and it’s excellent, but we all agree that the cinnamon rolls are the bomb and a must-have. We finish what we can of our meal and ask for more coffee. Our plates are cleared, and the four of us sit around chatting about anything and everything as we enjoy the rest of our coffees. I’m overjoyed to see that David seems to be having a fun time. My new friends are very welcoming, and I can tell they are enjoying his company as well.

  As the men are talking, I look around the restaurant and see that it is not as crowded as before. There are still a few people sitting around with their coffee, but most of the tables around us are empty. I check my phone. It is almost two-thirty.

  “You guys, we have been here for a while.” The three of them check their phones.

  “We have to make sure to give our server a good tip. We have taken up his table for a long time.” As soon as I say this, our server comes over and offers us more coffee.

  “Would you guys like more coffee or anything else? I just want to let you know we are closing soon.”

  “No. We are good. Sorry for sitting for so long and taking up your table.”

  “It’s no problem. I don’t mind.”

  “Okay, thank you. You can bring the check whenever.”

  “I actually have it right here.”

  We each pay what we owe and get up to leave. “Okay, guys, I will see you in the morning. Thanks for a fun first brunch experience. Everything was delicious, but next time, I probably only need to get the cinnamon rolls. I’m so full.”

  “I’m glad you enjoyed, it is a lot of food. Okay, you guys enjoy the rest of your Sunday and see you tomorrow Kell.”

  “You too. Bye, James.” I look over at David. “You ready to walk back home?”

  “Yep, let’s go.” As we walk down Belmont, I ask him what he thought of Vin and James.

  “They are both really nice. It was fun, and I’m glad I came.”

  I link arms with my brother and look up to give him a wide smile. “Good. I’m glad. I’m so happy you came with me.”

  Fourteen

  I have to say that there’s something that happens here in Chicago during the springtime. It’s only the beginning of April, but something truly magical starts to happen in the city. The trees and flowers come into bloom. One of the prettiest and well-known attractions is the beds of tulips, thousands of them, in varieties of colors that come to life along Michigan Avenue. It’s a sight to behold after the long cold months of Chicago’s winters. You can feel the city literally coming back to life.

  The city people have a little more bounce in their step. Strangers look up at you with a smile instead of down, heads buried between their shoulders, their gaze toward the ground. Happy chatter is all around. It’s the time of the year that instantly warms you inside, and you realize why you choose to live in this city.

  Chicagoans live for the spring and summer. They make the most of every moment, and for a good reason. The winters here are tough. I will follow all the girls’ advice and promise myself that next year, I will be prepared with the right boots, clothes, and a warmer coat. I have to say that once the weather changes you sort of forget about the last few blustery months and j
ust how cold it truly was. I love summer so much! I’m very excited for my first spring and summer here in the city.

  I check my email on Monday. Nothing from “Chocolate Chip Cookie Guy.” I feel relieved but also a little sad. I’m sure I hurt his feelings, and that wasn’t my intention. I go back and forth in my head about whether I should email him. I decide to email him to make sure he got back to Indianapolis okay. I ask if he enjoyed Chicago. He responds right away. He liked the city. He ended up hanging with a few people from the bar for the rest of the night, and he hoped I was feeling better. Yes, I’m much better, I tell him, and I’m glad he enjoyed the rest of his night. Okay, I now feel relieved. At least he wasn’t stuck being alone.

  The temperature is a high of fifty-seven degrees and sunny, so most of the office is leaving for lunch. Everyone wants to enjoy a warmer, sunny day. I’m at my desk thinking about what to do for lunch. I want to find out where everyone is going when I feel someone standing next to me. I look up, and it’s Vin.

  “You want to go for a walk and get lunch today? We could talk about some more projects that I might have for you.”

  I really don’t want to talk about work. I want to just get outside and enjoy the fresh air and sunshine.

  “Yep, okay.”

  “Well, grab your stuff and let’s go. I really need to get some air.”

  “Okay. I’m coming.”

  We walk out onto Michigan Avenue. I’m greeted with sunshine on my face rather than a blast of cold air. Oh, it feels lovely to be outside. The buildings are gleaming from the sun, and the Chicago River has a brilliant sparkle. It’s especially busy at this time of day. People all along the Avenue are wearing their coats open and smiles on their faces. They’re making the most of this beautiful day. We start walking without saying much. We are not in a rush, so we walk for a little bit longer.

  “So, what new projects do you have for me.”

  “Well, I was wondering if you would be interested in taking over all the billing and invoicing for the office. You are really organized, and it would be a huge help. James and I really don’t have time anymore.”