I've been undecided about that for years ... After gaining some weight, loosing it again, rinse and repeat for two of three times, I now know I don't want to be skinny ever again. Being at least somewhat bigger is way more fun. On the other hand, I also know that I will unlikely get very big unless I would be in a relationship with someone who supports and/or enjoys me bigger.
I can definately emphasize what LadyEjkua suggests: gain some, like 20-30 pound and see if you like it better then being thinner. Not just your personal preference, but whether or not you can tolerate the reactions of people around you.
12 years