What shall I do?

[ARainyNightInSoho]

I have a dilemma which isn’t really serious or a big deal but it’s paralysing me. I think because I am trying to stop being a people pleaser and this is the typical kind of situation I find myself in a lot. So I need objective advice.

Me and a friend (Anna) visit a mutual friend who lives abroad for a short break once or twice a year. Anna is a very last minute person with everything she does. She’s quite successful in her life but there’s a fair amount of chaos and resulting drama around her. Whenever we travel together I have to initiate arrangements and book. There is often a long period of procrastination leading up to this.

We are supposed to be visiting our friend in mid August. Flights are getting booked up, prices are going up and I just want to get things done, also so our friend knows exactly when we are coming. I have sent details of some travel options and Anna just replied with lots of questions. Yesterday she said she was too busy to book that day and today she says she’s ill. Normally I would patiently prod and wait for her to be ready but right now I feel like going ahead and booking travel just for myself and leaving her to book hers when she’s ready. I’d also like to avoid negotiating the journey with her as I want to take the most convenient route for me which isn’t inconvenient for her but probably not her preference.

From her perspective I think she will be disappointed that we possibly won’t be travelling together and that we haven’t had a discussion about the route. She will probably think I’m being impatient and unsympathetic.

Should I just go ahead and book now?

I would definitely book now and book just for myself on all future trips. I couldn't be dealing with needing to organise another adult. But I am impatient and unsympathetic so I don't mind Anna thinking that! She'd be right!

Yes but I’d explain what you’re going to do. Just be honest - ‘I’m finding this quite stressful. I feel more comfortable planning in advance and knowing what I’m doing. I hope you understand but I’m going to go ahead and book x arrangements for myself. Really look forward to catching up when you get there.’

@FloraBotticelli your advice does seem to be the right approach but I am certain she will then ask me to just wait one more day so we can book it together with the implication that I’m being impatient. She’s right that it won’t make a huge difference if we book tonight or tomorrow. It’s just a bit of a last straw situation for me. I’ve had to put up with her procrastination once too often. I doubt she realises that though. I’m always polite about it.

Yes. Message and say you’ve found a flight that suits you so you’re about to book and you’ll send her the details so she knows your plan once she’s better

If she asks you to wait say no, you prefer to get it sorted and are going to book tonight

Don’t give her the option! ‘This is what I’m doing’. Done. Don’t let yourself be so malleable.

Well, I suppose you need to decide whose discomfort is more important — your own or someone else’s.

Book it and don't apologise.

Why not just say “I’m going to book my flight tomorrow, if you are ready to book great, if not you can make your own arrangements when you are ready”

It’s fine if she’s not ready to commit, but you are.

In that case I would book it then tell her what you’ve booked. “Hey Anna I’ve booked a flight with x at x time on x day. Hopefully you can book the same so we can travel together! If not, see you there!”

Yes yes and yes book it for just you. If your friend wants to come and you have given her plenty of time, why should you wait around. Your are important to and you need to give yourself priority.

Exactly this. And don't give it another thought, you kindly gave her the details and didn't pressure her to do anything so she would be unreasonable to kick off.