When it comes to the multi-tattooed, such as myself, there will always be a special place in your heart for your first piece. I have absolutely no regrets about my first piece. It's a little eclectic, and it's easily the least intricate piece on me, since it was done over a 4-hour session with my friend (an apprentice at the time) in her boyfriend's loft. There's always a slight degree of almost-embarrassment about your first tattoo: you didn't know quite what the process was, and you didn't know what to look for in an artist; but that is not the same as regret. I love it as much as I love the work on my arms, and as much as I'll love every other piece I get in the coming years.
In my experience, tattoos are regretted because of a few reasons: getting tattoos while drunk, getting really shitty tattoos (i.e. poor quality), or getting something like a band name tattooed on yourself. That said, sometimes, right after getting colour done I'll look down at my arm and go "What have I done?"; that's only because at that point all the colour is muddied with my own blood. A couple days later it looks just as awesome as the rest of my ink.
In my experience, tattoos are regretted because of a few reasons: getting tattoos while drunk, getting really shitty tattoos (i.e. poor quality), or getting something like a band name tattooed on yourself. That said, sometimes, right after getting colour done I'll look down at my arm and go "What have I done?"; that's only because at that point all the colour is muddied with my own blood. A couple days later it looks just as awesome as the rest of my ink.