Over the last few weeks we’ve finalized our summer 2026 plans and started booking our flights. Summer in the Northern hemisphere is an expensive time to travel, so naturally my inner accountant was activated. A board meeting of budgeting neurons was called, the staff passionately stirred up to find creative ways to make this cheaper. Concluded with a bang of the calculator, the inspired neurons were sent off to fire away while I’m trying to sleep.
Airline miles, airline credits, bank points and deal-notifying Apps were rounded up and booking began. While we will normally jump at a good deal, we try to fly with one specific airline. They have some of the most convenient flights in and out of Cayman, and we have status so it saves us money with perks like free bags and seats.
Unfortunately
this airline has a bizarre flaw in their booking system that does not allow you to book your flight with an infant in your lap. Instead you need to book a flight for two and then contact customer ‘service’ to add the child to your booking.
This ridiculous rigmarole which does not appear to be a thing on other airlines, means speaking to a poor sod who is following the most annoying script of long winded flattery. I prefer to use a text chat because I can’t stand holding a phone to my ear for long periods of time, listening to heavy headset breathing, or the worst royalty free music an intern could find.
Over the week I ended up chatting with multiple customer ‘service’ team members to add our daughter to multiple flights. I also had to use credits, another unnecessarily complicated task, likely in the hope you give up in frustration and never use them. I’m sure they have a high success rate.
After booking our last flight with points I began a chat one last time to have our daughter added to the flight.
The Last Conversation
starts with an over zealous greeting from Parikshit - not a made up name - filled with promise on how happy they will be to help. When they notice I am a status holder, thanks and appreciation are heaped upon me for my existence.
Being the efficient, non-chatty type, I try to get straight to it with what I need. Infant added to my flight that I should have been able to book myself, and all the information they need to make that happen. I jump in the shower while Parikshit gets to work.
When I get out of the shower, Parikshit has realized my flight was booked with points and asked if they can transfer me to the only person who can handle such a bespoke request. Instead of doing the transfer, Parikshit waits a few minutes for a response and decides to close the chat.
I start up the chat again, and just my luck get reconnected to Parikshit! I confirm that transferring me to somebody who can get my daughter added will indeed be helpful considering that’s the reason I’ve started this chat in the first place. They shower me with praise on my status and ensure me they are very happy to help before reviewing my previous messages and finally transferring me to Ravi.
Ravi is also extremely excited to serve me, and is also very appreciative of my loyalty as a status holder.
They ask me to confirm the information I have provided only minutes ago to Parikshit, in messages they can apparently read. I repeat myself. He is thankful for the information.
As an aside I discovered over my many times going through this exercise with different team members that they can actually see what you’re typing in the chat BEFORE hitting send. How creepy is that!?
While Ravi gets to work on this complex task of getting my baby ticketed, he wants to know how my day is going so far. Considering I’ve spent three hours arguing about flight credits with previous customer ‘service’ team members I kindly refrain from answering that question.
Updates follow in five minute increments.
I’m assured that he is still working on it for me.
He’s contacting an ‘internal team’ — I thought he was the expert?!
I am thanked for my patience…
Again I am thanked for my patience… @#$%&!
Finally he confirms, “I have added the infant on your reservation, and you do not need to pay any fare for the infant.” Praise be!
“Your satisfaction means everything to us.” That seems highly unlikely Ravi but thanks for the heartfelt canned messages.
My P(doom)1 is probably on the high side—especially when I see companies replacing people with machines. But after experiences like this I say go ahead, let the robots have their turn. Lord save us all.