Confessions: My Friend’s a Serial Lowballer — What Do I Do?
When “let’s split evenly” becomes a controversial statement.
Let’s face it: mixing money and friendship can be super awkward. We’ve all got that one friend who “forgets” their wallet or bails when the check drops. With everything from food to rent costing a fortune, those money tensions can feel like a massive, unspoken elephant in the room. The problem isn’t just about dollars and cents, but also about fairness, boundaries, and respect.
Why talking about money feels so awkward
Money conversations are often considered paiseh. We’re taught to avoid being too calculative with friends, so when someone crosses a line, calling them out feels uncomfortable. There’s also the fear of ruining the vibe since no one wants to be the person who brings up money when everyone else is laughing over dessert. Add social FOMO into the mix, and many of us would rather quietly pay more than risk drama.
But avoiding these conversations can backfire. Over time, resentment builds, and friendships turn sour. Think about the friend who agrees to split the Grab fare but goes radio silent when you send your payment request. Or the cafe-hopping friend who doesn’t order but happily munches on everyone’s fries, then quietly skips their share of the bill. These “small” things pile up fast.
For Rachel Lim, 34, the ship in some friendships did not sail:
“I had friends who acted like they were broke, but they actually have money … They used my sympathy for them to indirectly ask for a free meal. I also had friends who always claimed that they “paid extra” but in reality, they paid less and tried to use that excuse as a cover-up. … [The] trust is gone once I … [found] out the truth.”
But not everyone had such a bad experience. For Dillon Foo, 22, he’d chase back his money. “If they [are] too broke to pay, [I’ll] treat them and when they’re better, they [would reciprocate].”
Stayed at an Airbnb in Bangkok with my travel kakis. Thankfully, money hasn’t been an issue for us.
Spotting the signs
Not every friend who owes you money is intentionally freeloading. Sometimes people genuinely forget, or they’re going through financial struggles. But when a pattern emerges, it’s worth paying attention. Here are some common types:
The perpetual moocher – Always borrowing but never paying back.
The split-dodger – Magically disappears or has to “leave early” when the bill arrives.
The luxuriously stingy – Will splurge on themselves but baulk at sharing costs, like the one who raids the hotel room’s minibar but “forgets” to chip in for snacks.
The group chat ghost – Never contributes when planning group gifts or events.
Recognising these patterns early helps you decide whether it’s worth having a conversation or it’s time to set firmer boundaries.
Ghosting group conversations.
How to tackle money conflicts without the drama
The key is to balance tact with clarity. If it’s a one-off situation, starting with a soft nudge can do the trick without sounding confrontational. Humour works well if your friendship allows it, too.
For group outings, tech is your best friend. When planning a staycation or group dinner, create a Google Pay group, or use budgeting apps like Splitwise so everyone sees their fair share in black and white. This takes the emotional sting out of chasing for money and avoids awkward moments.
Low Siew Yan, 27, thinks it depends on the amount owed and the friendship:
“If it’s a close friend and it’s small sums, I’m ok with it. If it’s a significant amount, provided they are financially stable but they intentionally don’t pay back, I might avoid having a meal with them or covering their share next time. [We] can still be friends, but nothing related to money anymore!”
Sharing a dim sum meal with friends.
Setting boundaries without losing friends
If someone’s behaviour is becoming a habit, it’s okay to say no. You don’t always have to cover for them or “lend” money if you’re uncomfortable. For instance, if a friend keeps dodging Grab fares, you could suggest taking public transport instead. It’s subtle but sends the message.
Otherwise, you can also opt for lower-cost hangouts like kopitiam sessions or hawker centre brunches, if you know certain friends tend to “forget” when the bill comes at pricier cafes. Setting boundaries helps ensure your own comfort and fairness without sounding too calculative.
For local finance influencer Daisy Anne Mitchell, here’s what she would do:
“I always act with the mindset that if I am paying for a bill first, on behalf of others, I should expect to make a loss. If everyone pays back what they owe, great! But if someone doesn’t after reminders, or there’s a few dollars discrepancy, I take that loss and just take a mental note to not pay upfront when that person is involved for the future.”
If you’re still keen on lending money or offering to pay first, here’s a piece of advice from Daisy, “Something I learnt from the hosts of The Receipt Podcast … is that if you’re giving your money to someone or something, you’re giving it without the expectation of it coming back.”
Whether you are navigating adulting, side hustles, or the rising cost of living in Singapore, it’s normal to feel sensitive about money. But handling these moments with both empathy and assertiveness ensures your friendships stay strong without leaving you feeling taken advantage of.