Most Helpful Guy
As long as you get tattoos for yourself, then it's just a bonus if somebody else likes it. I have playboy bunny tattoos on my arms, and especially now with that Playboy show on TV, I'm embarrassed since the bunny logo is everywhere, on commercials, billboards, etc.
Don't sleeve up just for him, since worst case you'll have a very visible tattoo that you may not really like.
BTW, I got the bunnies in part to impress a girl...she got married earlier this year to another guy, but I'll always have these bunnies to remember her by :o