How to make friends in the city

The truth is, we all want to magically garner people into our lives in a matter of snaps. HOWEVER, the universe likes to play the hardship game in the friendship department -especially for inner-city dwellers. 

Hey gents!

Can I hear an “oy”?

Making friends in the city can be extremely taxing (both emotional and physical). But in all seriousness, who can relate with me?

To all you metropolitan readers out there, I feel like we’re all on the same boat, no?

Dwelling in the city like wannabe fluent free birds, roaming with uncertainty. Sitting at a newly-discovered coffee shop, alone, wondering how the table across established a solid squad in the city. 

Those moments when you wonder if people will ever approach you, or perhaps feeling like the city hates you and blame it on retrograde…

Well brother, that’s incredibly absurd.

It takes a certain kind of push to get the ball rolling. Whether that be a stingy realization that you have to approach people manually, or the idea of weeding out any sort of checklist for the “perfect friend.”

…because let’s be honest, that perfect friend does not exist. You’re not perfect, and the same goes with the rest of humanity.

I think one of the best things about friendship stimulates from the fact that people acquire different tastes and backgrounds. Hence the phrase “acquired taste.”

One of the tricks when meeting a potential friend is to avoid scratching the similarities, and rather, scout the singularities that make the other person stand out from the crowd.

So many times we try and find common ground right off the bat in order to continue to “phase two”, which is great in theory…

Here’s a no-brainer example. Think of the movie Mean Girls (of all movies, I know 🙄). Wouldn’t it be odd if everyone looked like Regina George or the popular jock in school (what’s his name again…)?

I mean dang, that would be extremely BORING.

God created us to be different in our own ways, our own quirky ways. You can be friends with a fellow football fanatic, but that doesn’t guarantee the same body build, skin tone, love for beer and video games and so forth and so on.

Maybe he’s a low-key softie with a knack for reading? And happens to be a football player back in college?

You never know! And that’s what I love about friendships.

So first order of business: be open to all personality types and appearances. Once we tackle the challenge and meet people outside the usual preference, then the possibilities are endless.

Back in primary school and college, 99.9% of my friends were preppy. My lady friends donning their maternal pearls at the age of 18, incessantly talking about spin class, and my guy friends sporting Peter Millar horsebit loafers while bantering football lingo. 

It was fun while it lasted, but the entire thing felt so monotonous and transactional (also not enriching may I add). Simply put, I was in a bubble, surrounded by barbies and kens (and keep in mind I was the only asian of all my friend groups, oy).

Now that I live in a bigger city, there’s better opportunity for diversity. I need a bit of culture and challenge in my life. To try new things.

Here are three tactics I used to make new friends in the city:

C o m p l i m e n t i n g   S o m e o n e ‘ s   O u t f i t  
This is probably the most awkward of the trilogy. I breathe fashion, and when I see a stunning outfit, I share my thoughts. Believe it or not, sweet compliments shape people’s outlook for the day. We live in a society filled with noise and negativity, so sharing a sprinkle of zeal can be a potential highlight for someone. Once I compliment their clothing, I immediately ask for the brand, follow-up if the company is having a sale on that particular clothing, and start a full-on conversation!


B u m b l e   F r i e n d s 
I’m not one top take stupid risks; but in this case, feel free to call me stupid. I originally used Bumble as a dating experiment for the blog (I know, how terrible of me). However I recently found out about the friend and business features #gamechanger. I think it’s neat to find people within your proximity who are on the same boat as you (aka looking for friends). Like I mentioned earlier I typically try to find people who have various quirks (aka not your usual beer and sports dude). Once I find a match, I typically start with a “Hey man! How’s it going? What’s your favorite thing about XYZ city?” Make sure you use punctuation marks, like exclamation points and question marks to sound more inviting. Asking a random question afterward kicks off the conversation to a good start. 
Like any app, there’s always a downside. You’ll get sketchy weird people with other intentions, and all you have to do is report or ignore. The app doesn’t show your last name so you should be all good!


J o i n i n g    A   S m a l l   G r o u p 
As you may have already gathered, i’m a proud christian. One of the things I regretted back in college was not plugging into a small group. Finally, I found a young men’s group that meets every Thursday night.  Joining a small groups is a great way to instantly find people you can vibe with. It gives you the immediate chance to meet people without going through awkward situations (like the latter two options, lol😄) One of the benefits is finding people with similar values, but may have different backgrounds and interests that can help you grow and see life more diversely. Aside from the connection aspect, you also get deep conversations throughout the meetings. I love hearing and sharing struggles within the group and confiding with them, even though I barely know 40% of them lol. 
As a rule of thumb, when joining a group, make sure to keep a positive outlook and welcoming spirit. It’s never attractive to find a snobby, snappy individual. Ask random questions, giggle, and stay present!

Here’s what not to do…
D o n ‘ t   B r i  n g   U p   C a r e e r s 
No offense, but asking someone’s job and/or college major is simply an unattractive move. There’s more to a person than their job. It also makes you seem like an incredibly superficial and boring person (generally speaking). I’ve had many people ask me that question during the initial meeting, and down the road I realize they’re your stereotypical financial people who only care about money and “worldly success.” I know that’s not everyone, but just try to avoid this question overall. You can ask that question later on, but for starters, don’t do it. Similar to asking a lady’s weight during a first date, brining up careers is definitely a turn-off. 
S t a y   A w a y   F r o m   P h o  n e
This one’s a given, but let me sound like a broken record this time ’round. You guys, stay away from your phones when meeting people!! Being present and giving eye contact lets the person know you’re interested in them. Only bring up the phone when someone is calling, or when it’s time to switch digits. 
C o n s t a n t l y   F i  n d i n g   S i m i l a r i t i e s 
I get it, finding similarities is like second nature, right? It’s easier to befriend someone when you have things in common, but you have to understand this isn’t an audition to see who is most like you. Only seeing the mutual interests diminishes the other person’s unique qualities, resulting in possible issues down the road. It will force the other person in a state of impression, rather than self-expression. Obviously they need to be civil with upright values, but when it comes to personality and interests, exercise your curiosity and ask what makes them quirky. Challenge yourself to find people with different perspectives and try new things!


There you have it, friends. Some of my tips and tricks to jump in the friendship wagon. It’s hard, I know, but it takes guts. We all have muscles inside our body, some just take the time to challenge themselves and push their limits to enhance their muscles.
The same goes with friendships. Humans are designed to be with other people, and we just have to push ourselves and pursue people…no matter how hard or awkward) it takes. We’re all capable of finding friends.
You’ve got this!
all the brotherly love,


I'm Ian, the writer behind CharlesTucket (a mix between Charleston & Nantucket, two of my favorite places). My hope is to inspire every man to live a wholesome & whimsical life, one quirk at a time.


"Be watchful, stand firm in the faith, act like men, be strong. Let all that you do be done in love." | 1 Corinthians 16:13-14


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