Ok so me and my friend planned on putting new colors in our hair over our winter break. Problem is....he's pretty much a virgin (only had black hair once) and I have only used a crappy red dye that lasted a few weeks AND my hair is relaxed right now.

First help...is for my bud. He doesn't want to do just black again. I imagine black and red would look good on him (since it does on almost everyone) but I wasn't sure of anything else because his eyes change from a deep blue to a deep green.

And my hair has been bleached before and I plan on bleaching twice before I put any colors in (Deep colors don't often look all that good on me unless it is a red fading to brown). This summer I had pink extensions that looked pretty good and the summer before, my hair was red (dyed with shit so it was only bright red for a week or two). As much as I love reds and pinks....I was thinking of straying from them a bit. Any suggestions?

I think your friend would look good with a few chunks of green in his hair.
For you, how about a purple? I think you'd suit it and you might be able to go purple without having to bleach your hair.

Yeah I was thinking about black and something else. So just like green streaks or something?

I was thinking about trying purple but not sure of the shade. And over black won't it just be tinted?

Well, since you are bleaching your hair, I suggest a blue based green, such as Special Effects Sonic Green or Raw Green (available at Hot Topic). The Raw dye turns a lovely crayola green/emerald. It will contrast wonderfully with your skin tone. Also, Stay away from greens like Special Effects Iguana Green and Limelight, and Manic Panic Electric Lizard...they are too yellow and will look muddy.

As for your friend, I'd say a black/turquoise or dark blue/purple combination would be nice. It just depends on how daring he is. As for his color placement, he could do standard highlight streaks, or an undercolor (section his hair top and bottom, or a color block (focusing on his bangs)

Ah I thought your hair was still mostly red. If it's black then you'd definitely need to bleach for purple.
I think either a violet purple or a warmer pinkish purple would look good. If you can't decide which how about doing streaks of a few different shades?

wow thats a great idea. I was actually gonna do that with red if I was bold enough to bleach an underlayer and be blonde for a while.

I can't go green...my mom would kill me.....so when I hit 18 next year.....I shall give it a try. Basically I'm limited to reds and purples

SFX Nuclear Red and MP Vampire Red are awesome reds.

My favorite purple is probably SFX Wildflower -- it's my most frequently used and lasts for quite a while.