On the first day of our 4-day Bahamian cruise DD9 declares she hates sand and wants nothing to do with the beaches. (That’s the kind of info I’d like before choosing and paying for a beach vacation, my dear!)
At AK I rush ahead to stand in line for FOTLK and ask my wife to get me a Dole whip on the way to join me. We missed our chance to get one at MK and this would be my only chance. She gets one, but between the heat and rum it’s a sloppy mess by the time she makes it to FOTLK line. And just when she gets there they start moving the line inside, so my first experience with the Fabled Dole Whip Of Legend is this sticky, runny, yellow mess that I basically inhale in a rush, then get a brain freeze and have to throw it away to enter the theater. Not a lot of “magic” in that particular moment.
Two summers ago we joined my brother’s family at their family home in Virginia for a week-long vacation. It’s an old house situated on the Rappahannock river and we usually swim in the river, jet ski, knee board, water ski, etc. There’s literally nothing to do except the water. On the very first day my kids jump in, are promptly stung by jellyfish, and refuse to get back in the water. $150 in next-day deliveries from Amazon later they have body suits which make them feel comfortable in the boat, but they refuse to swim for the rest of the week. It was a pretty boring week.
In March I turned 40 and to celebrate I paid for my brothers, their families, and my best friends to join us at a cabin I rented in Indiana. I picked this place because the owner agreed to let me set off a 10 minute fireworks show as part of our celebration. I spent about $1200 on fireworks, spent 60 hours of my life planning out a show loosely synchronized to music, and spent the entire drive to the cabin alone in my SUV packed full to the gills with explosives. At the cabin, I spent the better part of an entire day setting up and wiring everything to my firing system. I must have done something wrong with the wiring because only about 50% of the fireworks failed to ignite, including about 75% of my finale. Now, the nice thing about fireworks is that things still went up and went boom, so the kids still thought it was great, but it was a total failure relative to the vision in my head, and I’m left with a shed full of unused stuff and no plan to get rid of it.
About 4 year ago we took the kids to Hilton Head. On our second day there, then-DS3 is getting into the shower, slips, falls, and hits his head on the metal track for the shower door. Blood immediately begins going everywhere. We freak the hell out, squads are called, and my son takes his very first squad ride to the hospital. My wife rides with him and I drive separately with then-DD5. By some miracle, by the time I get there (without the benefit of sirens), and park, and locate them, he has already had the wound stapled and they are working on discharge paperwork. I’ve never seen such fast turnaround. And by some additional miracle, DS3 is relatively unfazed by all this. We take him for an ice cream and then he wants to go to the children’s museum and it’s basically back to business as usual, except that he has staples in his head and my wife and I need to chug blood pressure meds like candy to calm ourselves down. (_If you’re wondering how this fits the “disappointment” theme, it’s mostly because I thought for sure I could weasel the Marriott out of some special treatment on account of my son busting open his noggin in their shower, but nope. They were extremely helpful and kind and supportive, but tight-fisted-AF when it came to any sort of “consolation bonus”.)
Oh, yeah, and then there’s the time that I lost $3000 in cash on the first day of our two-week New Zealand vacation to celebrate getting out of credit card debt. Long story short, we took a major trip to NZ before kids to celebrate getting out of debt. Upon landing, I converted all of our traveler’s checks into cash to cover all meals, entertainment, shopping, everything for 2 weeks. We went out to dinner and there was no safe in the room, so I put that envelope of cash under a couch cushion to hide it. The next morning we get up and start driving to our next hotel and 2 hours later OH HOLY CRAP I LEFT THE CASH IN THE ROOM. So, no big deal right, just call the hotel and tell them not to clean the room and go back and get it, right? Yeah, that’s what I should have done. What did I actually do? I called and said to the helpful desk agent “hey, can you go into room 123 and look to see if I left an envelope of cash in the couch?” And he says “sure”, and puts me on hold, and comes back 10 minutes later to say “nope, sorry bro, wasn’t there”. That’s when I realize that I’m the world’s biggest idiot and then spent about 30 minutes by myself in the car fighting one of the hardest mental battles of my life before ultimately resolving to enjoy the vacation anyway. In the end, we celebrated getting out of credit card debt by going about $3000 back into debt, and that desk agent at the hotel did whatever a-holes do with $3000 of stolen cash.
Good times all around 
