I can draw portraits, but it would be best if you did it via the guy thats going to ink it on you. here is a photo of one of my pieces. its a photo so it looks flat... but upclose it looks aight ...
Make a hard decision on the tattoo, ive been wanting to get one for 3years, but i waited till i got a design that i really wanted and would impact the situation in a special way. I'd Suggest no portrait, try like an angel holding a dove with like fancy writing that has D.O.B. and D.O.D. that way its meaningful and looks good.
everyone has to stop attacking his want for a tattoo. this isnt a topic saying "should i get a tattoo?" its a topic for people to help him get the tattoo that he knows he wants. i would help, but i dont draw anymore. good luck dude.