ASK HOLLY: ‘We don’t want our single, flaky friend to come on our group holiday.’

Welcome to Mamamia's new advice column, DON'T FREAK OUT, where Holly Wainwright solves your most personal and problematic dilemmas with her sage wisdom. If you have a drama you need solved, email us at — you can be anonymous of course because otherwise, awks.

Hi Holly,

I have a dilemma I need help with.

Two of my high school friends and I are planning a catch-up in Japan next year. 

We all live in different countries now and have not seen each other for five years. We have another friend who I know would be keen for the trip if she knew about it, but my mates don’t want her to be there because she’s hard to plan with and is a bit of a flaky person. I am the only one who has been in touch with her since leaving high school. 

Also, the three of us who are going to Japan are bringing our partners and my friend is currently single. I don’t want her to find out we’re going from someone else or social media. How do I tell her that we are going to Japan without hurting her feelings?

Thank you,

Guilt Trip

Watch: What a flaky person is like. Post continues after video.

Video via YouTube/DOMICS.

Dear Guilt Trip - You cannot. 

You cannot tell your single, flaky friend that you’re going to Japan without her and not hurt her feelings. 

In fact, if your number one priority is to not hurt her feelings, you can’t really go to Japan at all. 

Because the day you find out your friends are all going on holiday without you is a day for feelings. Maybe, your friend will only get the slightest twinge of FOMO, and move on with her day. Maybe your friend will tip into a full existential breakdown about why, why, why she is apparently such trash that her oldest friends can’t bear to spend a mini-break in paradise in her presence.

You are not in control of that. You are not in charge of her reaction. You are only in control of the delivery of the news.

But let’s be real. Your top priority is not sparing your friend hurt feelings. Your top priority is having a great time in Japan with your more easy-going old buddies and your partners who can all bond over being chosen, romantically and as travel companions.

And also, let’s be clear. That’s completely fine. You cannot live your life and make your YOLO travel choices based on the feelings of your old high-school friend. 

If you need further justification (you don’t) it’s also true that it would likely be quite awkward for Friend No4 to be overseas with two people she hasn’t seen since high school and their partners she’s never met. It could be a brilliant, easy-going, melting pot of joy. Or it could be a punish. And, reading between your tactful lines, when you say “She’s hard to plan with and is a bit of a flaky person”, what you mean is, that it will not be a brilliant, easy-going, melting pot of joy.


So no, you can’t go to Japan without hurting your old friend’s feelings.

BUT. You can go to Japan without being a total d*ck about it.

The elephant in your email is galumphing right through these words: "The three of us who are going to Japan are bringing our partners and my friend is currently single."

It’s also your loophole. 

This is not an old high-school friends’ catch-up, this is a couples’ holiday. And I don’t want to burst your bubble, friend, but no single person - whose life is full of freedom and possibility and adventure and autonomy - really wants to go on holiday with three couples alternating between bickering and pashing, compromising and manically scheduling. They don’t want to watch you and your loved one spending 20 minutes on whether to share the Bento Box. This, for a single person, is not a Fun Trip.

Here’s the trick to difficult conversations: Get as close to the truth as you can without being brutal.  

So you have to call your friend and be honest. Say something like: “Hey, Flakey. I didn’t want you to be surprised to see that Me, Popular 1 & Popular 2 are going to Japan with our partners next year. You know I’ve wanted to go for ages, and so has Brian/Betty (or whatever your partner’s alleged real name is).” End of.


If you mean it, you could add a, “Maybe you and I could plan a weekend away later in the year.” But don’t if you don’t.

Also, don’t say “I felt awkward about telling you”. Or, “I know you’ll be upset, but…” Basically, don’t say anything that pre-supposes how she feels about it.

Then you let her have whatever reaction she’s going to have. And you say as little as possible. You only get to hang up if she’s screaming at you.

If you are allergic to phone calls, this could be a text, but only if your dynamic is exchanging ‘real’ information in texts. 

If she tells you she’s upset, you say you understand, but this is a trip you want to do with your partner. Be kind. Be nice. But be straight up. 

Deliver the news. Go to Japan. And live with the possible hurt feelings of your friend. 

Or maybe your own, when she tells you she’d rather eat a box of hair than spend a week in Japan with you, two mean girls, and three strangers. Could go either way...

If you have a dilemma for Holly, please email

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