Search Results: how should i cut my hair

I picked the closest photos on Google, to my hair color, skin color, lips shape, but nose shape don't match with the first girl girls. Rather the second one.

I have always had the same style since I was 11 (the first one). Never shorter than this. Instead, it was sometimes much longer till my arse. Also, I have never dyed my hair, and that's out of question as I will never change my hair color.

Now I am very bored and feel like the first hairstyle is too teenager-ish for mya ge (28). I want to make some changes.

Which do you prefer? Should I keep current one or try the new one?

I've had long hair all my life and I'm wanting a change. What does everyone think I should do. I'd get it cut to near my shoulder blades or longer.

Also, comment why you think so and what I should do.

Does this mean he is into me? This Middle Eastern guy, and I say his race because M. E men don't like black woman like that. I grew up in the middle east; I know. I'm not attractive but I don't think I'm ugly, per se.
Anyway, this dude, he's 26 (Im 20) and I worked together on a lab, we share the same Bio class. I had seen him a few times and had started a conversation with him or two. To the point that I know his name, favourite sport, job, and age. He reminds me of a puppy.
I think he's smart and he seems to be friendly. He has implied that he thinks I'm smart in a conversation about how I might have gotten a 100% on a quiz while everyone got a 90%. I got an 88%.
I dont think he has a girlfriend and it seems that I can make him smile and laugh. As far as I am aware, he listens to me.
He's has moved closer to me be when we work, though I am sure he could see where he was. When I go back to my original group to finish my work, he "looked" around for me. He came over and hugged me, and told me he had to go. Also, he let me take off his hat (not a turban) and mess with his hair. He asked me if I liked his hat and I said I did but I want to see his hair more. He said has to cut but I told him that next time to expect him to be without his hat.
He said, "I got you."
Does he like me?

Hi, I have really long here I tried to post photo where it's obvious but I only have black shirts and my hair is black so I hope you'll see. Yes, should I cut it and / or change color? Behind is until my butt in front of is let's say until belly