Going to dye my virgin hair o_o Can anyone with hair dye experience help me out? ;~;

So I'm doing my hair for the first time....EVER. This is a big moment for me xD

I've been growing my hair for about 6 months now after I got my asian mullet, which is basically very very short layers on top that stop at my chin, and then its long hair, makes it look like extensions. The hair that frames my face was also cut short so it falls along my face with my bangs so I really wanted to grow those out before dying it >.<

I want long pretty hair now lol Here's a picture of the growth:



I CHANGED SO MUCH IN A FEW MONTHS...I lost weight too! xD But ahem, back to the subject.

I want to get this color:



I think that's like a red wine? >.< This is where your advice comes in haha
I'm really not sure...

But if I wanted to get this, would I need to bleach my hair?
I really don't want to...I hear its damaging ;~;
My hair is already pretty dry because my hair is naturally wavy so I heat style a lot :I

Is there a hair dye that isn't very damaging you can recommend? And is it possible that I don't have to bleach my hair?

Also, my mom suggested I use henna to dye it since its natural and not damaging but I don't think I can get that color...or can I? ;~; I dunno...HELP.