I've just come from having lunch with my friend, T.  She and I have been friends for a VERY long time, ever since 3rd grade.  I have to admit, I could not take my eyes off her hair because it's...absolutely...HORRIBLE.   :P

She keeps it cut short (argh) but that's not the problem.  The thing is the shape is just awful for her face.  It's cut right below her ears and she combs it straight down--so that it bows out over each ear.  It's-it's just HORRIBLE.  Terribly unflattering.  

My question, as her friend, do I tell her how unflattering this cut makes her look?  Or do I suck it up and keep my mouth shut?  Keep in mind this woman already has little confidence in herself so, in all honesty, I'm not sure she could handle blunt truth.  On the other hand, what if she "wakes up" one day, realizes her hair style sucks and goes, "Why didn't you tell me?!"    :-/

...*looks poised to start talking, then stops, starts, then stops*... This can be very dicey. Like you said on the one hand you feel like you should tell her because she's your friend and you want her to look and feel good about herself. On the other hand you worry about hurting her feelings/confidence. I will not give you advice only support, it's a catch 22 a situation I found myself in, (I believe I did nothing, there was another friend involved and I have no idea if she said anything or not, I think I just forgot.  :-[) I tend to be brutally honest and that doesn't always go over well.  ::) I'm sure you'll get plenty of great advice from others on here though.  ;)

this is kind of tricky, depending on how your friend receives input. maybe you could mention a hairstyle she's had in the past that looked really good on her, and ask her if she's thought of growing it back to that? if you say it's horrible now, she may have a hard time putting up with it while it grows to something else, then again, if she thinks it's great she may continue to cut it that way.

Absolutely keep your mouth shut.

Our friends are not perfect, Trish. And what if she actually likes her hair just the way it is?? You'll not only hurt her feelings at the time, but she will hear your words echoing in her head for the rest of her life.
   Since the 2 of you have been friends for a very long time, your opinion will have more weight than just the average Joe's and she will take your comments much more personally.

A little over a year ago, the guy that I was involved with got a new haircut that I really didn't care for. He asked my opinion on it and I tried to be as politely honest as possible. Though he put up a brave front, I could tell that he was upset that I didn't dig his new 'do and I felt pretty crappy about it.  :(

But this woman hasn't asked for your opinion. It's quite possible that she actually likes her hair as it is or really doesn't see it as that big of a deal.
   I understand that hair is an important thing to you. You've been through a lot with your own. But it might not be that important to her.

You're probably thinking, "but she's my friend! I've known her so many years, surely I'm inclined to be upfront with her! And isn't it counterintuitive to not be honest with myself and others at all times?!"
   You know what? Be honest with yourself. That's fine. Hate her hair if you must. Scream about it into your pillow if you must. Rave about it to your clothes, pets, dishes, etc. in the privacy of your own home, but absolutely keep it private. If one day, she consults your opinion, then it would be ok to gently and politely express it while choosing your words verrrry carefully. But until then, zip it.

Focus on the great person that she is and how lucky the pair of you are to have both kept a friend for so many years rather than the superficial details.
If one day she does "wake up," change her mind about her current style and ask you why you didn't tell her, you may then smile politely and answer, "Because I'm your friend."

I side with Angel.  If she hasn't asked your opinion, don't give one.  You would hate to lose a friendship over hair.

Angel Spun has covered all the important things to consider so well that I don't have anything to add and I couldn't have put it as well either.  You may not think her hair looks great but maybe she does.  You wear your hair the way you prefer to wear it and I think it's best to assume that others wear their hair the way they prefer to wear it unless they state something else or ask you for your opinion.

I also agree  :-X .. say nothing unless you are asked for an opinion. As we all know, hair is a sensitive subject!

After thinking about this for a while, I want to add that.. though you should avoid making direct comments about your friends hair, maybe it would be nice to share some of your own hair secrets or tips. Perhaps she just doesn't know how to care for her hair properly. Maybe even tell her about your favorite hair forum  :)

i guess i was thinking of how i'd want my friends to tell me if my hair were ugly...but maybe the others are right. don't tell her unless she asks, and then do so carefully and tactfully.

You know, y'all are right.
She did NOT ask for my opinion/advice and I should (WILL) keep my mouth shut.  
I'll simply keep taking good care of my own hair and serve as a silent example.   8-)  
Thanks for the advice, everyone.

Wise choice, Trish.  ;)