I was 30 before I got my first (and only) tattoo. It had to be something that meant something to me.
So, I spent a week with my best friend in Houston. She wanted to go out one night, so I told her, "great! let's go!" Well, she wanted to go to HER hangouts, and she thought I'd be too uncomfortable with it. I tried assuring her by telling her I'm not only cool with going to a gay bar with her, I'd even wear HER underwear! She didn't believe me.
Well, she took me shopping, as my clothes (5.11 pants and a polo shirt w/ desert tan boots) weren't "acceptable". So we're at the mall, and she's picking out clothes that made me look... uhm... "metrosexual". Well, I'm trying on these clothes, and I popped off, "you're trying to make me look like a gay guy!" She said, "I knew it! You're not cool with this!" I laughed and bought the clothes. I mean, hell, I didn't know anybody, and thought I wouldn't see these people again! Penny loafers, khaki socks, some nice slacks, and a button shirt with a thin black dress belt: $185.
So we're getting ready, and while she was putting on her makeup, she came out of her bathroom while I'm rummaging through her underwear drawer. "What are you doing!?" she asked. "I'm looking for the most comfortable pair of your underwear I can put on my fat ass!"
So I see these Superman boxer briefs. Ah ha! Got 'em!
Well let me tell ya! Boxer briefs for chicks are DEFINATELY made differently than boxer briefs for dudes! I had a great time, but I was UNCOMFORTABLE ALL NIGHT! But, I'm a man of my word.
So, I had a great night with my best friend in a gay bar. The next night, it hit me what I wanted for a tattoo...
The next night, she and I went out to the tattoo parlor a good friend of mine owns and I got it! You shoulda seen the look on their faces when I gave them her underwear to scan for the job
The moral of the story is, there's no harm in waiting for getting the tattoo that has the meaning you're looking for.