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I'd like to be born on a far away planet rich with resources of a peaceful race that is still powerful enough to ward off those that would take advantage of our peaceful nature. I don't really have a preference regarding gender because nobody would give a crap about my gender in this world. Perhaps in my race we are genderless/asexual! I would like to be born in an age that interstellar travel is not only possible, it's also very readily available, fast, efficient and accessible. Due to the time in which I live and the richness of the resources, professions would be much more whimsical. The necessities of life would be taken care of by a safe yet artificial intelligence (or just replicators or something) and that would leave my race to focus on the arts, socialising and exploration. I'd probably dabble in all three - exploring new and beautiful places with my friends and loved ones and being inspired towards creating worlds of my own by these adventures.
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Ten more years and I get another week of vacation. I'm good.
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I'd want to be a hot woman so my original male self could find myself hot. I realise this wouldn't really work though since the original me wouldn't exist to appreciate my new look.
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I'd either choose to be someone rich and famous so I can have everything I want and a legion of loyal fans who argue with people on the internet over all the trout that comes out of my mouth.
Or I'd be more or less the same and would just look like the girl in my current avatar and profile pic. Maybe add internet celebrity status to that...
Not sure which. I just know I'd be an American in both scenarios.