A year alone in space.
Would you rather spend a day at the beach or a day whale watching?
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A surgeon
Would you rather be a life time virgin or incompetent in bed and fail each time?
incompetent in bed and fail each time
How difficult is sleeping anyway?
Would you rather eat chocolate cherry ice cream or caramel pecan ice cream
(it's 30 C here today -- your answer is important)
Tricky question as male, but I don’t like Trump. So it will be Cruz 
Would you rather swim in a swimming pool or in a lake?
In a swimming pool
Would you rather be with a philanthropist who supports the wrong cause 80% of the time or a misanthropist who makes the right decision 50% of the time?
Of course, those percentages should make you think a bit 
Philanthtropist
off: how can you like a swimmingpool better?! you have to turn every 30seconds, you cannot relax and swim for half an hour in one line, there is no sense of accomplisment like you have after crossing a large lake. Also Chlorine and red-eyes because of the chlorine gas that forms when people pee in the pool!
Would you rather break your little toe or your smart phone?
My smart phone for sure!
Would you rather be in prison or an island untouched by civilization but seemingly friendly?
island untouched by civilization but seemingly friendly
Would you rather play darts or blackjack?
blackjack
would you rather have chronic fatigue or chronic pain?
==> fatigue not meaning sleeping 12hours a day will make it right, but more beeing so tired you are not able to shower without (feeling you're about to) faint(ing), being to tired to sleep, etc.
Illusionist
Would you rather fail at an audition and try another time or fail while performing having the audience disappointed in you?
High dude. Drunk I can't perform ♦
Would you rather smoke too much weed or take a small amount of xtc on a weekly basis?