How to make friends

By | December 2, 2015

Forewarning, my dear reader, this article is not about finances. It fact, it almost runs counter to good finances, as it may entice you to spend more. I’m going to tell you about it anyway because it ended up being the best thing I ever did.

In April 2015, I started a project I called, “Operation Enjoy the Crap Out of Sydney While I Still Can.” I’ve mentioned it on my blog several times already.  This not-at-all classified operation entailed me making plans to do something Every Single Day. My rules were simple.

Operation Enjoy Rules

  1. Plan something fun to do every day.
  2. The “something” must be outside my apartment if I’m by myself.

And this is how I discovered the secret to making friends. Ask people to do things with you.

Okay, so maybe this is obvious for the rest of humanity who seem to know exactly what they’re doing on this giant rock hurtling through space, but this realization changed my world. Prior to starting Operation Enjoy, and after living in Sydney for more than a year, I had three close friends that I spoke to regularly and another half-dozen acquaintances that I spoke to sporadically. By the time I left Sydney six months later, I had a dozen close friends that I spoke to regularly and another dozen acquaintances.

This was not an easy transition for me because, at my core, I fear I am a socially awkward, shy, introverted, reclusive hobbit.

Don’t get me wrong, I think I’m friendly enough and I can make friends when the making is easy and convenient. I cherish the close friends I had in my insulated middle and high school. The dozens of booze-filled networking events in law school made making friends comically simple.

reclusive hobbit

But in the “real world” outside of school and as an adult working a job that demanded too many of my hours, I found making friends extremely difficult. Post law school in Chicago, I tended to socialize with family who lived close by and were roughly my age. When I moved to Sydney though, I did not know a soul and while that thought delighted my misanthropic tendencies, it terrified the much larger part of me that despised my misanthropic tendencies.

When I feel nervous, I tend to put on my lawyer trousers and research my way out of the anxiety.

Apparently, there are three conditions that are crucial to making close friends:

Conditions that are crucial to making close friends

  • Proximity
  • Repeated, unplanned interactions
  • Setting that encourages people to let their guard down and confide in each other

The first bullet point was easy enough to conquer. Sydney boasted more than 4 million humans in “close proximity” to me. Surely, I could tolerate and eventually even like a handful of them.

The third bullet point was also fairly simple. Like much of the world, Australia’s culture relies heavily on the imbibing of alcohol. If that’s not a setting that encourages people to let their guard down and confide in each other, I don’t know what is.

This frog doesn't understand either.

The frog doesn’t understand either.

The second bullet point was the one that wrecked me. The repeated interactions part I understand as the number of interactions I have with someone determines which box in my brain – friend, acquaintance or stranger danger – they should crawl into. The “unplanned” bit though had me stymied. Real life isn’t like television. People don’t just drop by unannounced.

Okay, so it’s one thing to understand empirically how to make friends (which I still didn’t) and it’s another to actually put it into practice. This is why I liked Operation Enjoy so much. Per my own rules, I HAD to do something every single day. I exhausted my “close friends” pool fairly early on so I reached out to acquaintances more often. Eventually, my acquaintances turned into close friends. When I exhausted my “acquaintances pool,” I felt compelled to reach out to new people and expand my social circle.

I found this life changing because research shows that good relationships are a key aspect of happiness. And more importantly to me, it WORKED. I felt happier. I felt more at home in Sydney. I constantly had something to look forward to. My journal entries were perkier and more interesting.


I would print out a weekly calendar and a monthly calendar, look at my various lists (Australia Bucket List, Operation Enjoy Ideas, etc.) and slot in activities. I would then invite people to do them with me. On the inevitable days when nobody I knew could accompany me, I struck out alone and struck up conversations on public transportation, at meetup events, at bars and restaurants. I would get phone numbers of people I found interesting and invite them to do things with me later.

I just realized this smiley face looks kind of worried.

I just realized this smiley face looks kind of worried.

If it’s not obvious by now, I’m a big believer of measuring your goals. I “measured” Operation Enjoy with my resolutions chart. If I followed the rules outlined above, I gave myself a smiley face. I loved getting those smiley faces. As an added bonus, on the occasional days when my plans fell through, staying in felt like an indulgence and not like I was a loser with no social life.

And guess what? I finally understand that part of the research that stymied me years earlier. The more I asked people to hang out with me, the more people asked me to hang out with them. Eventually, eventually, eventually my closest, closest friends would text to get together impromptu.

I know this doesn’t fit the thrifty mantra I’ve been spewing around here, but I am all about spending your money on experiences. Go experiences, go!

Tips for making friends as an adult

  1. Ask people to do things with you!!
  2. If you’re moving to a new city, announce it on your social media and ask the people you trusted enough to friend on the Facebook if they know anyone in your new city.
  3. Ask people about themselves. Everyone has a story.
  4. Try different meetup groups. My meetup groups were the walking groups and the book clubs.
  5. When you meet a friend of a friend that you click with, ask for their number and then ask them to do things.
  6. Say yes when people ask you to do things.

19 thoughts on “How to make friends

  1. MrJones

    Great post! Id love to hear more about non-financial ideas from you!

    1. Thriftygal Post author

      Thank you for taking the time to comment! I appreciate the feedback greatly as I was worried this post would not be of interest to people. 🙂

  2. Wolf359

    This post really hit it home for me.

    Everything is not about the finances. A large part of being happy in retirement (early or otherwise) is the social interaction. You opened my eyes to some new possibilities on how to make friends and open up my social life.

  3. Aaron

    Hello! Just dropped by after reading the link on MMM. I love your blog, and this is my favorite post so far! Cheers!

  4. K

    Nice post. I’m a new empty nester, and needed this kick in the a$$. Smiley faces all around!

  5. Luckyvik

    Thanks for this post, I confidentially had asked some friends to go to a show this weekend and they said yes. Must do this more often!

  6. Joel

    Great post, I also came to your blog after reading the MM interview. In the YMOYL literature (maybe Joe or Vicki or someone making a post somewhere) I recall reading what was sort of a throwaway line in a larger essay about living in various places during life’s trajectory: “Happiness is relationships with others.”

    Your post makes me think I need to explore that throwaway line a little more.

  7. Mrs DN @ The Dollar Notes

    What a timely post. We are moving to Brisbane in some months (from northern Europe) which is very exciting but at the same time I know it will take time to get to know people. Previously it has been very easy for me to make friends but now I’m moving into a new country and culture so it will be a new experience. Making friends seems so much more difficult after you finish your studies!

  8. Mark

    Good post really enjoyed it. I am about ready to retire at the age of 59. And have found that I don’t have that many friends anymore. Sure My wife and I have a lot of acquaintances and friends that we see relatively seldom due to how busy we are. I am really looking forward to having the time to go do things with friends again .

  9. Caz

    Discovered your blog through MMM, but I wish I had discovered it sooner when you were still in Sydney. I would have invited you to hang out, raid my library, and make some potato (and onion) bhajis….

    As a born and bred Sydneysider it will always have a piece of my heart, but its no secret its not the easiest of places to make new friends.

    Thanks for your savings philosophy and advice. As someone who has a similar mindset but who gave up Big Law early on for the public service, it may take me a tad longer to reach financial independence but your blog is is certainly encouraging. I wish you the happiest of world travels!

  10. Cara

    Thank you for this post and all the recipes and great financial thoughts! I’m also a MMM referral, also a lawyer, also went through the “how do I make friends in a new city” conundrum. Can’t wait for more recipes!

  11. Andy

    Another excellent post. Loved it. I moved two time zones and over a thousand miles a year ago for a new job. I’ve had a tough time balancing all of my hugely lofty goals since then. Making new friends that live nearby always seems to land near the bottom. This seems like a great plan. *feeling inspired* Thanks!

  12. Renan

    I really like the way you write (even though English is not my native language), and this post is my favorite so far.

    Luckily my job (which I love almost as much as I love parentheses) is kind of a great source of friends.

    I hope you’re making good friends here in South America. Please keep up with great articles like this one. 🙂

  13. Martini

    Love the post! And the blog, another MMM referral. I’ve also just moved to Sydney and don’t know a soul, such a paradox surrounded by people but totally alone. I also wanted to comment to see if it was the blog or the commenters that left all the ‘i’s out from every word.

  14. Roy

    You demonstrated that something as important as friendships, can be measured and given high priority, thanks for that idea, Roy


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