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Been there done that, 3 times actually:
Fell in love with JA on first trip in 1995. On the morning of our planned departure from T-Water Beach Hotel we just couldn't do it. Called AA and extended from 5 days to the maximum possible of 8 days. (Had a plane to catch back to Europe from New York on day 9). 
Second extension was of sixth trip in 1999. After 3 weeks in Jamaica, I got one of those legendary ear infections and had to stay another week. However, nobody talked me into this or sent me to the doctor. Only got myself to blame!
Third extension was of trip #20 in 2010. Again after three weeks in Jamaica, I just felt I needed another few days. So that time I contacted my boss and let him know I was staying 4 more days. 
Seems like the longer my trip was, the harder it was to go back home. :-) Usually I am staying between 10 and 17 nights and make it back home as planned. Except for the very first time (5 days were just too short) and on the two occasions I was staying 21 nights. lol
These days I am travelling with my baby boy. He is 16 months now and has already seen Jamaica 3 times! His trip #4 will be my #26, hopefully this coming October.
Btw, on my 25 trips, there was one occasion when the airline was looking for volunteers to stay behind... Hotel paid for until next available departure date. Did not dare to accept, because I had still been quite new at my job back then. Of course when I told the story at work afterwards, everybody said I should have done it!
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