How to make friends in Chicago: sit outside a starbucks by yourself

I finally made my long anticipated move to Chicago. I just got a job in the city and am actually starting to get settled here.

It’s been a crazy past couple of weeks and my mind has been going in every which direction trying to figure out the city and what it is that I want to be doing. Last night was one of my lowest points since I’ve moved here. I was in the city and had to say goodbye to someone that I care very much about. The reason why it was such a big deal for me, is because I have no idea when I will see him again. On top of that, I just generally felt lost. I haven’t had a chance to see any of my friends (besides him) in the past month, and I haven’t really made many here yet. I just feel lonely. I am also stressing out about my job, because I have to commute quite a ways and I’m not sure if it’s going to work out yet.

Anyways, I was visibly upset and didn’t want to go home yet, so I sat down at a starbucks and ordered a coffee. I sat outside with my headphones in, drinking my coffee alone and watching the thousands of people pass by on Michigan Avenue when a complete stranger approached me out of no where. I took out my headphones as he extended his hand and introduced himself. He asked me to dinner and I quickly declined as I still felt full and sad from wallowing in my self pity. He then asked me, “Well what about a drink?” I paused for a second and thought to myself, why not? What else am I going to do, sit here and cry about how alone and lost I feel? So I said yes.

We made our way down the street to an upscale Mexican restaurant and we both ordered a margarita. Aside from it being the best margarita that I have ever had, the vibe of the restaurant was amazing. There were fireplaces made up of blue rocks on fire everywhere, the lighting was dim, and every one around me seemed beautiful and happy. He ended up ordering tapas even though I insisted that I wasn’t hungry. Over our margaritas and tapas, we discussed our life philosophies, what we looked for in other people, using Tinder in the city, and work. It was great conversation for it being with someone that I had just met less than an hour ago. We ended up parting ways, but before we did, he gave me his business card (so adult). I haven’t reached out to him yet and I’m honestly still not sure if I will.

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As I rode the CTA home that night, I felt extremely hopeful. This is the beginning of my new life. I may feel completely alone one moment, but I am surrounded by hundreds of thousands of people every single day. There are so many people who are going to be a part of my life here that I simply just haven’t come across yet. Last night made me realize that in this city, anything is possible. And if I want something, I need to put myself out there and go get it. Because at this point, the only thing that’s stopping me is myself. Here’s to a new city, a new outlook on life, new friends, new loves, and most importantly new experiences.

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10 minutes to Linden

I had expected to get to your new apartment in the city & for so much to have changed. I expected you to be different. I expected everything to be different. But not much had.

So many things were the same. The way that we acted towards each other. Your bed and light blue bed sheets. The jokes that we made with each other. You’re laugh and the smell of your skin. 

That was the first time that I had seen you in 8 months. Not that we haven’t stopped talking, I hear from you every now and then & we still snapchat pretty often. I’m not really sure how I feel about everything yet. I mean I did just leave your apartment an hour ago, but I’m curious to see how I’ll feel when I wake up tomorrow. I’ve been waiting for this night for months on end. Not this particular night I guess I should say, but just to see you in general. I had so much to say to you that I didn’t get to express, but I’m not worried. Something tells me that this won’t be the last time that I’ll see you. Something tells me that there will be many more nights like tonight. But part of me isn’t even sure that I still want to tell you all of the things that I had previously planned on saying to you. For so long, I thought that you were it. But something about to night makes me feel like maybe you’re not. Like there’s so much more out there for me and I need to focus more on myself. I need to try new things and meet new people. Possibly fall in love with someone that’s not you. For the first time in over a year, I’m more excited about what’s to come for me, rather than what’s to come for us. 

3 years from now 


I always have a hard time trying to imagine myself and where I’m at in life in the future, because I’m a very spontaneous person and I tend to just go with the flow. But for some reason, lately I can’t get the image of myself living in Chicago a few years down the road out of my head. I can imagine myself hopping off the train after a day at work and meeting a friend in the city for some coffee or a bubble tea. I imagine myself wearing blazers and heels and with shorter hair; more mature. I imagine myself having new friends whether I met them on a night out or at work. I see myself stopping at a food stand downtown to get a bite to eat while shopping on michicagn avenue. I picture Monday mornings on the busy street trying to hale a taxi so I’m not late for work and summer days in big floppy hats that are spent on north avenue beach. I picture myself with a guy that I met while living in the city and he opens doors for me and knows my coffee order by heart. I’m not sure how reasonable it all is at this point in my life, but I know it’s what I want. I was just saying that I feel like I have nothing to look forward to in my life right now, but maybe this is it. My overall goal is just to be happy. But I think this one might be 2nd. Even if just parts of it come true, I’ll be happy. I’ve never felt like I belonged where I grew up. As much as I love my college town, sometimes I still feel like I don’t belong here either. But there’s something about Chicago that I’ve always loved. Even though most of it is foreign to me, it doesn’t always feel that way. I truly feel like I could live there and be happy.

Goal #1 is to be happy. And #2 is to find somewhere that I feel I truly belong.

I think it’s time to start over.

I haven’t written on here for awhile. I got pretty sick about 2 weeks ago and went to Chicago to stay with my sister and nephew. The whole time that I was there, I felt more at home than I have in the past two years. I wasn’t longing to be somewhere else. I didn’t feel forced to stay where I was because I was avoiding being somewhere else. It felt so great. I forgot that feeling. Of feeling comfortable and at ease wherever you are. It made me seriously consider moving there after college. I wish that I could now. I almost wish that I had never signed a lease for next year already. More than anything, I just want to pack up and leave. Get far away from everything and everyone that I know and start over. Because I’m so unhappy here.