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Why travelling with friends can lead to meltdowns and broken friendships artwork

Why travelling with friends can lead to meltdowns and broken friendships

The Straits Times Podcasts

September 14, 2026

Is travelling with friends worth the risk when all hell breaks loose? From disagreements over budget to one person wanting to “travelmax” while another wants to wake up at noon, a trip can become a horror story.

Speakers Sue-Ann Tan, See Kai Wen

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Sue-Ann Tan (0:04)

Will you travel with friends?

See Kai Wen (0:05)

And risk your entire friendship?

Sue-Ann Tan (0:07)

I say yes, he says no, let's discuss. Hi, I'm Sue-Ann.

See Kai Wen (0:10)

And I'm Kai Wen, and you're listening to Headstart Nuggets. Small talk around big problems.

Sue-Ann Tan (0:14)

Okay, so Kai Wen, will you travel with friends, and when was the last time you travelled with your friends?

See Kai Wen (0:19)

To be very honest, the last time I travelled with my friends was 7 years ago, and I am not somebody who is very keen on travelling with my friends, because I have heard a lot of horror stories.

It never goes out of the group chat. So that's one thing, and I always feel like travelling with friends is a little bit troublesome, because number one, I have to plan around everybody's idea of what's a holiday, and then my idea of a holiday is getting watered down, but I'm paying the same price, mind you, as I go with myself or with my family.

Sue-Ann Tan (0:48)

And taking leave.

See Kai Wen (0:49)

So I just feel like it's so much hassle, and it's easier just to be travelling with your family or my partner.

That's how I feel. I know you like to travel with your friends.

Sue-Ann Tan (0:59)

Yeah, that is so interesting because the last time I travelled with my friends was like May.

And I always travel to far-flung places like UK, US, that kind of thing. Yeah, and we actually want to travel again together.

See Kai Wen (1:11)

And UK is so high commitment. It's like money, leave.

Sue-Ann Tan (1:14)

Yeah, but I think to me, it's like, oh, if I go on my own, it's a bit hard to do these places solo, and I don't want to drag my family so far as well, especially if they're not super interested. And I think my friends and I will have the same interests and hobbies. We like to go to museums.

We like to go to bookshops. We like to drink tea. We go to cafes. So I think our idea of a holiday is quite similar.

See Kai Wen (1:36)

Okay, wait, and is it the same friends? Like you always call the... You always ask the same friends to go on holiday.

Sue-Ann Tan (1:41)

Yes, it's the same like travel gang.

See Kai Wen (1:43)

So with a group, like a travel group.

Sue-Ann Tan (1:44)

Yeah, like my travel group. But that's not to say that it's easy, right? Because I mean, from the first thing, when.

When you want to go, already that's a problem. You know, we try to plan it around public holidays, but sometimes it's like, oh, I can't make it.

See Kai Wen (1:56)

Wait, you guys are all in different industries.

Sue-Ann Tan (1:58)

Yes, exactly. So, and we all have different like, budgets.

See Kai Wen (2:01)

Oh my god, yeah.

Sue-Ann Tan (2:02)

We have different preferences in terms of like, comms, flights, that kind of thing.

See Kai Wen (2:07)

So troublesome, right? Yeah, it is.

Sue-Ann Tan (2:09)

Okay, I must say that you need to be willing to compromise. And you need to be willing to...

See Kai Wen (2:12)

That's the word, compromise.

Sue-Ann Tan (2:13)

state upfront what you want. Because I think if you go into it, and then this person says like, I want to fly SQ. And in your heart, you're like, actually no, I only want to fly Cathay or something.

Then you don't voice it, you just keep it, keep it, keep it. It's going to be so much worse. It's better if you just state upfront. And then we either compromise or just stay separate flights lah.

See Kai Wen (2:33)

And everybody is okay with differing views lah. That means you're not going to say like, okay, so let's say if somebody says, I only want to take scoot, you're okay to compromise, even though you are at SQ level of compromise.

Sue-Ann Tan (2:42)

Yeah, I mean if maybe it's a short flight, they are like, okay, scoot is fine. You tell me like maybe 7 hours, no food, I'm like, maybe you take scoot yourself, and then I meal there.

See Kai Wen (2:52)

Okay, that's true. So this topic is very interesting to me because, like I said, 7 years is a long time, right? Honestly, you know when you start to hear so many ghost stories, you believe that ghosts are real.

Okay, so I have this story to share. I've heard that this group of people, maybe about 10 people, so they all came from a uni club. So it's like those kind of CCA. So people are like very hyper after the activity. They just like, oh my god, we are so close. Let's just get out there and go somewhere.

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