On Chicago

By | May 23, 2016

I know I’m always yapping to you about how close friendships are important to happiness, but research shows that my yapping is vital. Life is better when you have pleasant interactions with people on a regular basis. That’s one of my “duh” realizations.


Found in Santiago, Chile

I’ve been shoddy with my posting schedule this past week because I’ve been hanging out in Chicago. Chicago! What a crummy, wonderful city you are. I do love you. I’m sorry that I don’t always remember that. Although it’s 50 degrees here in May. Can you blame me for forgetting? And your public transportation smells. I know that’s not unique to you.

I love Chicago so much because I don’t have to try here. I can make last-minute plans easily. I know where I enjoy eating.* I run into people I know in the streets. I don’t get (as) lost (as easily). I have close friends and awesome family in this city. Close and awesome people I don’t have to try with.

Granted, I have met awesome people everywhere I’ve ever been. The world is overrun with awesome people waiting to meet me and, more importantly, you. The only difference with the people in Chicago is the length of time they have reminded me of their awesomeness. Understand that friends come and go, but with a precious few, you should hold on. Work hard to bridge the gaps in geography and lifestyle. Because the older you get, the more you need the people who knew you when you were young.

Also, vocal similarity. When I open my mouth, I sound like people in Chicago. I am not automatically labeled a foreigner.

So if you haven’t found your version of Chicago yet, or, if you’re like me and you have your Chicago and your Sydney and your NYC, but you’re a greedy bastard and you want more, here’s a specific step-by-step guide that worked for me and might work for you.

I may have mentioned meetup.com before. I met people in Sydney using this site, mostly through book clubs and walking meetups, but there are meetup groups for everything. I went to a Mr. Money Mustache meetup last week because apparently those exist. What a world we live in! Here’s what you do:

How to make friends through meetup.com

  1. Go to meetup.com and find some groups in your area within an appropriate radius of where you exist.
  2. Pick a group that sounds interesting to you.
  3. Attend a meeting.
  4. Attend another meeting.
  5. Maybe one more.
  6. When you’ve discovered people you enjoy interacting with, swap information.
  7. Invite them to do things with you.
  8. Do things with them.
  9. Be friends.
  10. Keep going to the meetup too. You’ll meet more people.
  11. Repeat steps 6-8.
  12. Make more friends.
  13. Ask the people you feel most comfortable with to do things with you spontaneously.
  14. Have close friends.
  15. Enjoy life.

The El.

I can make that list much longer, but I feel that way about most of my lists. For instance, if you don’t enjoy #3, go back and make sure you judged #2 correctly and the event is something that actually interests you and not just something you think should interest you.

#6 could theoretically happen after #3 or #4. With some people, you will click right away. With most people however, I’ve found you will need a couple of interactions.

During #8, let your guard down and confide in these new potential friends. That gets you to #9. The book I linked to as my “research” on happiness at the beginning of this post is Scott Adam’s book “How to Fail at Almost Everything and Still Win Big.” I read this book recently while on Chicago’s smelly transportation and I enthusiastically recommend it. Not only does he agree with the idea of index funds, he has some great thoughts on happiness and food and exercise and life in general. On friendship, he writes:

Research shows that people will automatically label you a friend if you share a secret. Sharing a confidence is a fast-track way to cause people to like and trust you.”

That quote doesn’t need much explanation, especially with the citation he provided and I subsequently linked to. Sharing a secret makes you human. Empathy. He has some advice that I love.

“I also find it helpful to remind myself that every human is a mess on the inside. It’s easy to assume the good-looking and well-spoken person in front of you has it all together and is therefore your superior. The reality is that everyone is a basket case on the inside. Some people just hide it better. Find me a normal person and I’ll show you someone you just don’t know that well. It helps to remind yourself that your own flaws aren’t that bad compared with everyone eles’s.”

It takes time and effort to figure out what activities interest you, seek them out, do them, find people who you tolerate, hang out with them, decide when to show off your basket and repeat the whole process. I find it to be mostly worth that time and effort though. Good friendships are a key component of happiness.


Near the corner of Adams and Wells (This amuses me because I have a friend named Adam Wells).

*I don’t tell you to buy things, but Chicago has Taza! This restaurant has the best falafels in the world and I ate there often when I worked nearby. The owner recognized me after 2.5 years away, using my name and proclaiming I broke his heart with my absence. He gave me a free bottle of water.

Chicago represent!

8 thoughts on “On Chicago

  1. Vivek @ LifeAfterFI

    The book (How to Fail at Almost Everything and Still Win Big) looks quite interesting…. Added it to my reading list 🙂 Thanks for the recommendation!

  2. Ally

    Omg-you’re in Chicago? Did you go to Ferris Fest?http://www.today.com/popculture/ferris-bueller-s-day-turns-30-chicago-throws-best-party-t94126?cid=eml_onsite
    Chicago is a great town: lots of culture, lots of good restaurants and great interesting neighborhoods, and good corner bars you can go to after a night at the opera.
    I will take your point to heart about friendships, especially your quote of Scott’s basket case comment. I have seen mention before of the self-disclosure rule; it is good advice, because that is how you move from acquaintances to buddies, unless of course your disclosure freaks them out. Time and place. Time and place.

    1. Thriftygal Post author

      @Ally, no didn’t make it to Ferris fest. Great movie though. And yes, time and place indeed!

  3. Jason

    About half way through the book, loving it so far! Thanks for the recommendation!

  4. Classical_Liberal

    I found my chicago, then foolishly left for greener pastures. By the time I realized what I had lost and returned, either it, or me had changed. The big change was the people (including me). Everyone & everyplace that is awesome constantly evolves (or they/it would never have reached awesomeness to begin with). When someone finds a place that is truly home, live in the moment and enjoy. When it or you change, don’t waste time regretting what is lost, rather relish the times had and make the next “chicago”.

  5. zeejaythorne

    Making friends as an adult is not as hard as so many people think – if you live in a city. Showing up for folks. Finding folks with similar interests. Then showing up some more.

  6. Steve

    I like how you push going to a meeting and then going to another meeting. The hardest thing about Meetup is not just going to that first meeting, but keeping the ball rolling. But then it gets easier! A lot of people give up if the first meeting doesn’t meet their expectations.

    PS – love the blog 🙂


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