The Ways That Being Awkward With Money Has Ruined My Life

For some inexplicable reason, I find the topic of money excruciatingly awkward. I don’t want to chat about splitting bills, or rent, or about the $20 I owed you that one time. Money is weird and intangible to me and it seems to be a taboo topic in polite conversation. I wish I never had to think or worry about it.

However, much to my chagrin, cash indeed rules everything around me (thanks a LOT, WuTang) and in my efforts to ignore it as a serious thing, I have burdened myself with financial awkwardness.

Here are the specific ways I have ruined my life by being awkward about money, and what I should’ve done in the first place:

Buying rounds that nobody even asked for

This goes first because it happens the most frequently. My brain, four drinks in, turns me pushy and over-confident. I think, ‘Here we are at this swanky uptown bar and everybody wants another drink and I’m going to be the hero that buys it for them! That’s me: everyone’s best friend! The kindest person in the world! A Princess with a pocket full of gold!’

But here’s the thing. I am not any of those things. I am just a scrappy, inner city writer with a felt cap and a jacket full of holes. I eat lots of beans out of steel bowls with my left hand. The bike I ride ‘round town is rusty. Shame spirals are always bad, but they’re especially bad when they cost you one hundred dollars and you are also hungover.

What have I done?!

What I should do: Buy a bottle of orange juice and hide it under my shirt. Pour it into glasses and walk them over on a tray. Tell people there is vodka in them. Accept all glory and praise. Or I could just suppress the urge to buy a round and buy my own drinks at the bar.

Buying dinner for my friend to avoid the weird pay dance

It’s a tale as old as time. It starts with, “I’ve got this one”, followed by “No, no, you can’t”, supported by an “I insist” and then continues on like so for six hundred long years.

These fights about who pays can get brutal: while on the outside, I’m begging for my friend to let me pay, my insides are screaming out for a large, wise bird to descend unto the restaurant, dig their talons into my shoulders and fly me away. My screams of, “But I’ve got to get this one…” will disappear into the cool night, as will my guilt about needing to pay in the first place. I can’t tell you how many times my bank account has been dangerously close to zero, there is no bird to save me, and I still insist on picking up the bill anyway.

What I should do: Slip away to the bathroom just before the meal is over and don’t come back. Sure, the friend is now confused and stuck with the bill, but I’m already on a bus to Alice Springs and have papers confirming my name change. Alternatively, we could just split the bill and pay for roughly what we ordered.

Buying coffee for people in the office

Asking people if they need a coffee when you’re heading to the café anyway is almost mandatory. What kind of monster goes on a solo coffee run? Then has the audacity to enter back into the office sipping their flat white in front of everyone else? A monster, that’s who. Oh, I already said monster? That’s fine. It only makes my point stronger.

So many times in my life, I have found myself in a situation where a coworker takes me up on my offer and I buy them a coffee and they forget to pay me back. But I never forget. No sir, not me. Not this poor young chap in the felt cap.

Yes I will get that for you.

What I should do: Pretend to take a phone call, walk out of the office, buy a coffee, drink the whole thing at the café (quickly, it doesn’t matter if my throat burns), make my way back to the office, and pretend to finish up on the call. I could also, should someone take me up on my offer, ask for the $4 beforehand.

Rounding down the amount of money people owe me to seem “chill”

Say if I bought concert tickets for my friend and they were $63.50, a normal person would request that their friend transfer them $63.50. Whereas I, noted Money Queen and Haver Of All Wealth, insists on rounding down the figure. I have no idea why. Do I think I’m too good for that $3.50? Do I think people will start calling me a “cool girl” because I didn’t hit them up for those extra dollars?

The deep sadness is that I’m really not too good for that $3.50. It’s a cup of coffee to keep my poor hands warm on a cold winter’s day, because the worn out, fingerless gloves I wear don’t seem to do the trick anymore. I truly do this rounding down thing so often that I wouldn’t be surprised if I’m rounding myself out of hundreds of dollars.

What I should do: Round up, if anything. Test the limits. Try $10 extra, $20, $40. $300. Be a huge jerk. Or, just tell them the actual amount that it cost.

Donating to fun runs

Oh, god. You know how they say Facebook gives us all anxiety? I actually think Facebook is fine for me a lot of the time; it’s just a whole bunch of articles and whimsical cooking videos I accidentally watch the whole way through. But the minute I see a friend or family member posting about raising money for a fun run, I break into a cold sweat.


When I see those posts, I can’t ignore them. And these people never stop posting. I’m all but forced to donate. And it’s not like a gold coin donation, either. Some start at a $50 donation price! If I had $50, I’d be including vegetables in my grocery order, not giving it away to a charity. I am a charity! But I can’t be the only person at a family gatho who hasn’t contributed to my cousin’s colour run.

What I should do: Ask to join the fun run with my friend. Create my own donation website and fall ill on the day. Keep the money for myself. I also have the option to only donate what I can afford.

Lead image: Bridesmaids, Universal Pictures.

Josephine is a writer from western Sydney who likes to blatantly lie on her bios. She played the youngest sister in 80s sitcom Family Ties and looks fantastic running with a backpack on. Follow her on twitter here.

Want to start saving?

Open a Westpac savings account to take control of your money.

Find Out More