Don't DO IT!
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We'll when we stayed in a hotel for a few nights after our cruise, there was no way we were going to stay in a standard room, I mean we had just been starring at the ocean for the 7 days prior. So I told Jay "ask for a complimentary upgrade, and see what they say." Ask and you shall receive, we went from a small room with a view of buildings, to a huge room with an awesome ocean view. We were so happy, it would have been over $500 dollars more if we did it ourselves. We passed some rooms that should have been ours and we were "like no way we deserve the upgraded room"! We have been too spoiled! Now next time we get a hotel room we will think twice about getting a standard room, we'll say "hey, why not, last time we got a bigger, nicer room for free so why not splurge this time if we can't get it complimentary again"!
We are screwed with car rentals too, when I booked us a car I booked an economy car. I mean what does it matter what we drive, we will be in Hawaii. We'll at the first Hawaii island rental car pickup (out of 6 total different days of renting through Dollar Rental), the lady really liked us and gave us a 2 car upgrade complimentary. We should have had an Eco but we were styling instead in a nicer car! Well at the next island we went back and forth about" should we just pay for an upgrade, it's way better and last time we did get it for free! The lady at that place ddin't like us as much and wouldn't upgrade us for free. So, We we stood our ground, we decided being in Hawaii was enough, we didn't need to spend the extra money, the car is just going to get us where we want to go and then we will hardly be in it! Well that lasted until we got in the Eco, we started the car up, sat in the parking lot, then turn off the car and went and paid for a 2 car upgrade! We did that for the rest of our trip! So ultimately they made their money back and some!
We are also ruined for flying, on our way back from Hawaii we asked for exit seats, well the lady went above and beyond, and ultimately hurt us and will cost us $1,000's of dollars in the long run! She upgraded us to premier seating! It changed our life and dramatically improved our flying experience. Sitting in premier makes flying ALMOST fun! What a difference! I don't know what we will do for our next vacation! Trust me, what you don't know will not hurt you, so please just take the cheapest way of vacationing possible and DO NOT ask for a complimentary upgrade, in the long run they will ALL get their money back and some!
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