'Are you sure you can afford it?' — the hardest money question to ask your friends artwork

'Are you sure you can afford it?' — the hardest money question to ask your friends

The Straits Times Podcasts

August 3, 2026

Talking to friends about money can be sensitive, here’s how to navigate it.  Synopsis: Every first and third Monday of the month, get a head start in your personal finance, career and life with The Straits Times.
Speakers: Sue-Ann Tan, See Kai Wen, Vivienne Ong
**Sue-Ann Tan** (0:04)
Do you know how much money your friends have?

**See Kai Wen** (0:06)
Have you had to ask your friend repeatedly to pay you back for that meal?

**Sue-Ann Tan** (0:09)
And more importantly, will this change your friendship with them? Hi, I'm Sue-Ann.

**See Kai Wen** (0:12)
And I'm Kai Wen.

**Sue-Ann Tan** (0:13)
And you're listening to Headstart On Record. In the studio with us today is our guest, Vivienne Ong from MoneyOwl.

**See Kai Wen** (0:19)
Welcome Vivienne!

**Sue-Ann Tan** (0:19)
Hi! Nice to meet you guys! Hi! So thanks so much for coming on, and I think we'll just get right into it right?

**See Kai Wen** (0:25)
Let's go!

**Sue-Ann Tan** (0:26)
Like, will you ever share your salary with your friends?

**Vivienne Ong** (0:29)
Okay. So, when I first started out my career, right? When you're all fresh grads and you all start from the same playing field, then I'll ask my friends, hey, how much do you get for your first job? And I would share my salary. I can share it right now. My first job, 24K.

**See Kai Wen** (0:43)
Wow. Very transparent.

**Sue-Ann Tan** (0:46)
That was like 10 years ago.

**Vivienne Ong** (0:48)
But I think as you get older, and then I think it starts getting a bit tricky because then some friends, they suddenly start earning a lot. Then some friends, their careers don't progress as much. And I think after that, we stop sharing because then there are feelings of maybe jealousy or awkwardness. And I think now we don't really share our salaries. But last time when I was younger, yes, definitely.

**See Kai Wen** (1:10)
I think it's that comparison also with your friends. And then like, who is doing better, who is doing worse, you know. And then like, who is right now the alpha of the pack.
I mean, okay, unfortunately, money is the easiest way to signal your, how well you're doing in life. And then if you are, if you are paisae, if you feel bad about, you know, a certain thing, then you won't bring it up lah. Yeah.

**Vivienne Ong** (1:32)
I think especially if your friends are like uni-mates, or like poly-mates, right? You all start from the ground up. But then how come one friend is doing way better than the other? There's bound to be feelings of resentment. And you just don't want that in a friendship.

**Sue-Ann Tan** (1:43)
Yeah. Do you think it will ruin dynamics in the friend group, if everybody knew each other's salaries?

**Vivienne Ong** (1:49)
I think it might.
Depending on how the friend group is set up, right? So I said like, let's say if you know each other from, let's say from school, and then some friends are doing a lot better than the others, then it's bound to create some friction. Especially if let's say, you know, you have a lot of… a group of like 5 girls, right? I'm from a girl school. So secondary school, 5 girls. You go out for an expensive dinner. Then you say, let's split the bill equally. But what if one person is earning way more than the other?
And then, it might create a bit of friction and tension. Especially if you know, actually that person is earning 15k a month. Why can't they just cover the bill? Why must they be so calculative and split the bill equally?

**See Kai Wen** (2:33)
What do you expect though? Like let's say, if you know your friend earns like 15k, 20k, and then you are just like, okay, we just started 3, 4k. Is that an expectation? Right.

**Vivienne Ong** (2:43)
Really, really? I think it's a-

**See Kai Wen** (2:45)
Is it a fair expectation?

**Vivienne Ong** (2:47)
If the friend chose the place and the place is an expensive place, then I would be like, hey, can we go for a cheaper place? If they say no, then...

**See Kai Wen** (2:58)
Yeah, Sue-Ann, I think you have stories to share about that.

**Sue-Ann Tan** (3:01)
It is sensitive, right? Because like, I have attended like a friend's birthday dinner, and at that point, some of us were students, so our income was zero, and some of them were like working. And then the bill came out to like 160 per person, and they were like, let's split equally. So at the point, what can you say, right? It's like, oh, this is somebody's birthday, you know, it's a celebratory event.

**See Kai Wen** (3:23)
And you didn't choose the venue.

**Sue-Ann Tan** (3:24)
But I didn't choose the venue, and I also feel like, oh, my income is zero at this moment.

**Vivienne Ong** (3:30)

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