TIFU by planning a surprise vacation without checking if my partner could actually go

A few weeks ago, I made what I thought was a grand romantic gesture, and it totally backfired. My partner has been completely overwhelmed with work for months – super long hours, constant stress, barely any time to breathe. I wanted to do something meaningful to give them a break, so I decided to plan a surprise vacation.

I’d recently come into a bit of extra money from a lucky win (one of those rare moments where something actually went right), so I figured, why not go all out? I booked flights, reserved a beautiful Airbnb right by the beach, and even lined up activities I knew they’d love – scuba diving, wine tastings, the whole nine yards. I didn’t tell them anything until it was all set, thinking the big reveal would be this amazing, movie-worthy moment.

Except… I never checked their schedule.

The day I showed them everything – complete with a cheesy slideshow of all the cool stuff we’d be doing – they looked excited at first, but then kind of froze. Turns out, they couldn’t take time off at all because of a critical project deadline at work. I was crushed. They were super sweet about it and kept saying they appreciated the effort, but I could tell they felt bad, and honestly, so did I.

To make it worse, most of the bookings were non-refundable because I rushed to lock everything in. I ended up losing a good chunk of what I’d saved, and now the whole thing is just kind of a sore subject between us. What was supposed to be a bonding experience ended up feeling like a misfire I can’t really undo.

TL;DR: Surprised my partner with a vacation without checking their work schedule. They couldn’t go, and I lost a bunch of money on non-refundable plans.