Yea, it depends. Some tattoos are pretty bad and I know that some people get them without thinking and regret it later. But if it's just 1-2 pieces that really fit you or symbolize you and you think it through, it can never get "old." But I mean... you never know. You may not think the same way about your tattoo as you did in you 20s. :D
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Absolutely. Time changes not only someones taste but also their body.