Most Helpful Girl
Have said this before. But get something you want on your body for the rest of your life. Don't get something really big unless you are sure. If this is going to be your first tattoo, I'd start off with something small. And if you can, draw your tattoo on with permanent marker for a couple months and if you're still not sick of it, keep it.
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Most Helpful Guy
Getting a tattoo is a big deal.
I've got a couple of tattoos and the only thing I'd advise you on is to make sure that whatever you select has some kind of meaning to you personally, something that you connect with on a personal level.
DO NOT GET SOME RANDOM DESIGN JUST BECAUSE IT "LOOKS COOL"
As for the pain, it depends on the location of the part of the body where you plan on getting inked.