From the Prompt from the DailyOM.com

The worst vacation was the one that never was. One year, in the late 2000’s, I scheduled a dream vacation for my family of five: my husband and three children, who’s ages were probably 14, 12 and 9; I’m just guessing here. I don’t remember those details as much as I remember the tremendous disappointment in excruciating detail. You see, I planned to spend New Year’s Eve in Times Square in New York City. It had always been a dream of mine and this seemed to be the perfect year for it. In doing my research, I discovered that if you wanted hotel reservations you had to make them by April. I definitely insisted that we stay in a hotel for this event because I wanted to have the comfort of my own warm space with a freakin bathroom! Plus, depending on the weather, we could literally watch from the comfort of our room. I didn’t necessarily need to be outside among the tens of thousands of people although that was the main plan. When I go to New York City I always stay at least one night at the Marriott Marquis, right smack in the middle of Times Square. It’s a high end, very fancy huge hotel and needless to say, very expensive, but I was pleasantly surprised at the rate I was offered as I made that early phone call in April. So much so that I decided to get two rooms for our family, adjoining of course. I made the plane reservations and that price was also reasonable for five people. The main caveat was that all of this was non-refundable which I totally understood and was fine with me considering the relatively low cost. I’m going to guess here, but I think the total airfare and rooms was in the range of $7,000 which is of course a lot of money but this was a bucket list dream for me and I wanted to have this experience once in my life, with my family. It would be something we would never forget. I think we planned on staying two nights, maybe three, and we would definitely plan to hook up with our friends Joe and Valerie and their two young daughters. They lived right across the Hudson in Hoboken, NJ and I’d visited with them often, every time I went to New York City. They were wonderful hosts during every visit and we would have been welcome to stay with them for free, but as I said I wanted the comfort of my own room and bathroom right in the middle of the whole thing.
The trip was paid for and anticipated for several months. Somewhere around October, I unceremoniously lost my job and therefore half of our income with no hope in sight for replacing the income I was earning prior to my being let go. I’d become obsolete in my position and it really shouldn’t have been a surprise in hindsight but I was gobsmacked. Truly horrified at this complete 180 of my entire career. I no longer had a career! I was probably somewhere in my late 40’s and could in no way retire so I had to find a job and given that I’d been with the same company for 25 years, and I didn’t have a college education, I knew that I would be starting from scratch at a low paying administrative/bookkeeping job. But that nightmare is a story for another time,
I distinctly remember thinking that there was no way we could take this longed-for vacation. No one but me really cared; Alan never wanted to go in the first place and the kids didn’t know what all the excitement of being in Times Square on New Year’s Eve was all about. We’d do something else for the holiday, something more reasonable. I felt like I had to take responsibility for this debacle and figure out a way to cancel this trip. I was beyond devastated. It went against every fiber of my being not to go, because I live by one of my favorite mantras which is that I only regret the things I don’t do. How could I give up this trip? I knew the opportunity would never come again (and it hasn’t and it won’t at this late stage of the game, some 10-15 years later; we’re definitely too old for this type of debauchery) so I had to try to get my non-refundable money back. I tried, to no avail. Both the hotel and the airline were having none of it, no matter how much I cried and begged. So I took it one step further: I called and wrote to, as I like to call them, Mr. Delta and Mr. Marriott directly, I went straight to the top of each organization and pled my case (knowing full well they could sell those airline tickets and those hotel rooms for quadruple or more than what I paid for them by this point). And I waited for the final answer. Was I going to be awarded the refunds and replenish our rapidly depleting coffers or were we going on this vacation with heavy hearts and a mountain of guilt?
I remember sitting in a Subway sandwich shop when I got the first call. “Yes, Mrs. Clapp, we will refund your money with no fees. We hope you can join us another time”. The second call came subsequently with the same answer. So what did I do? Did I raise my fist in victory? Was I proud of my going the extra mile (excuse the pun) to get my money back? No indeed, I did not and was not. I sat there in that Subway shop and cried. Not tears of relief or happiness. No no no. I cried like a baby because I wanted that vacation more than anything. And I knew now that it was never going to happen. Sure, we’ve taken fun vacations since, but this whole experience was such a shitshow that I never recovered enough to try it again. It is the one and only regret that I have in my life. The one thing I didn’t do. I’ve never gotten over it and I suppose in the big picture it’s not that big of a deal but I’ll never forget the huge ache of disappointment and I regret it to this day, even though it was of course the right thing to do,
Woe is me.