I have a lot. I started when I was 18 and thought they should all have meaning so over the years, got several "meaningful" ones. I stopped for years, no reason why. Years later, I started looking into tattoos again, went on a great forum and learned a lot about them, the changes over the years, and what was really available if you put the time and money into it.
I researched loads and finally booked in with an artist 60 miles away for my first large tattoo. Realising what art you could get changed my whole mindset. There are some good studios near me, but not in the styles I like, so I travel to collect from artists I love. I used to just go to a local studio, now I realise that unless you're very fortunate, the local studio probably isn't that great. I've travelled to other countries, been chosen by an artist to be tattooed for free at a convention as he'd heard about me from other artists and knew I'd sit like a rock. I was meant to be travelling several hours tomorrow to start my back piece but had to cancel - thanks train strikes!
Even the older members of my family who hate tattoos have recognised the artist's skill in the ones I have. I still have some of the shit ones but they're being lasered then covered.
I don't regret any of mine, especially not the ones in the last 10/11years since I discovered the art. The people I go to are so good they have waiting lists of 8months+ so plenty of time to think about it. I always allow free reign to do whatever they want as I have done my research and trust the artists. I have tried encouraging friends to do the same but some of them just want to get tattooed next week or whatever so go to their local studio and get something not that good, but if they're happy with it, that's up to them.
I think there are a lot of young people who are going for maximum coverages ASAP and so just book in with someone local without checking the tattooist's style works for what they want, ie they go to someone who specialises in neo-trad but then the customer wants Japanese. They just want cheap, cheerful, and to have it done now. Each to their own, but I think those are the people who will eventually regret them. If you invest time, money (decent tattoos are NOT cheap), and do your research, you will end up with a beautiful piece of art that will hardly fade and still look as good in 10 years as it did when you got it done. Go to a cheap and easy tattooist, your tattoo will scab (very bad to scab!), lose colour/be patchy, and fade relatively quickly.
Oh, and as to what they'll look like when I'm old and wrinkly....
Sorry for pontificating 😁 As you may be able to tell, I am very into tattoos!