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I have a tattoo myself, got it in Nov 2010, fair chunk of art in size, so far I definitely don't regret it.

I'm not gonna tell you that you should get a tattoo, but if you pick a design or whatever that you like and avoid getting names from lovers or whatever, you probably won't regret it

Also, my opinion on the family matter: YOU should decide to get a tattoo or not, don't let anyone (Even family and friends) lecture on whether or not you should.