I think your hair frames your face very well right now – I wouldn’t play with it too much. Maybe some highlights, like you’ve already thought of. Or a bit of a wave… don’t go overboard. Remember, if it ain’t broke (and it ain’t!), don’t fix it.
Then again, I’m a guy, so what do I know :o
I think I’m going to do it… a quick shower as soon as the laundry is done, and then up the street to a hair salon I’ve never tried! I’m going to a party tonight, so either I will look fantastic or terrible, depending on how well they cut my hair! I might be late to said party, though, but that’s ok. I’m hoping I’ll look good enough to make up for it.
I just need to figure out how to put what I want into words, and then also let them do what they feel would be best for me. I want basically ZERO prep time in the mornings, though… I have no skills whatsoever with any hair styling tools, even a hair brush!
Oooh, exciting. Good luck! Don’t forget to share pics of your new look!
Rhiannon, thanks for the info. I’m definitely going to check that out when the semester ends!
Kytheria, you should join us in our quest to make our hair not boring. 
tarragon, I guess the kind of style I’m think of is something like this. It’s a bit short, which is why I’m wary - I’m never good at taking care of short hair.
My plan is to go next Wednesday (after pay-day). At this rate I’ll probably end up plopping myself in the chair and asking the lady to do as she pleases.
Oh yes, that’s definitely the style my Grandmom’s hair was. It’s not that short, though, and it looks nice. Short, to me, is pixy cut. 
Good luck!
Oh, so bored! And my hair is only a few inches long, so there’s not much I can do with it. My sister finished chemo and radiation recently and her hair is just growing back. At about 1/2 in long all over it was so cute! She got tons of compliments on it. I wish I had the courage to cut mine that short.
StG
Bored and horrified. My last haircut made me look like Laura Bush, now it’s doing a Florence Henderson Brady Bunch kind of thing. Don’t know which I hate more. Mr. 'Addi and kiddoeaddi think I should grow it long again and wear it in one big braid, like I used to in my 30s. A suggestion I’ll probably ignore. YMMV, but I think long hair looks very strange on most women of a certain age.
Unless you guys can suggest something more flattering, I guess I’ll just have it bobbed at my softening chin line. 
Edited to add: HazelNutCoffee, you’re cute as pie.
Dude here, checking in. The stylist said I had “fun hair” last time I went in (it tends to be kind of wild and bedheady even after I wash it), and wanted to do something “a little weird” with it. I consented, and it was pretty terrible. She cut a lot of parts of it waaaaaay too short in weird asymmetrical ways that I could tell were supposed to be kind of artsy and punky, but unless I spent a LOT of time on it, it just looked fucked-up.
I’ve grown it out super-shaggy and am ready to start from scratch again.
I was bored with my hair so I got it done yesterday, blonde highlights, layered at the front with a long thin fringe (bangs). The fringe is annoying me at the moment.
I think your hair is fine as it is though, Id just go for some simple highlights if I were you. If you decide to go curly, Id keep the length, curly hair is so much easier to manage when its long!
Hey, there was an article in the LA Times today about a new fashion trend that may just suit you. You may have to let your hair grow out a bit more and get a very mild perm. It’s called post-rehab chic and you sort of keep your hair kind of unkempt with a super wide designer headband, plus the obligatory oversized sunglasses to hide your bloodshot eyes. It’s supposed to look like you just got out of jail after being on a bender, but fashionably so. You may have to bleach your hair while you’re at it.
Me, I need to get a haircut. I’m going to go to the bad side of town and try to get a $10 haircut from one of those latina hairdressers. I’m going for the Shaun White skate punk look. I don’t speak any Spanish so wish me luck!
I hate my hair. And I have been wearing it in a ponytail every day due to humidity, hot weather, and the need for frizz control, and I think my hair is falling out at a more rapid pace than usual because of that.
But I don’t know what to do. I have a very round face and a high forehead, and I’m not sure what’s the most flattering to that… (Also, what a knockout in your photo! ;))
lorene, I have to wear a ponytail when I go to work, so I have the same problems. How do you handle it?
Thankee for the compliements! Darryl, err… I don’t think the blonde I-just-got-out-of-jail look is very… flattering, ya know? 
Plus I don’t want my students to get the wrong idea. Heh.
I told my friend I wanted to get a perm and she looked at me as if I’d sprouted a second head and told me that salons don’t do perms anymore. Is this true?
[chanting] HENNA . . . HENNA . . . HENNA! [/chanting]
Seriously, henna rocks. And it’s effects can be so stunning-yet-subtle on black hair. (Or it can be dramatic, depending on what you use.) Plus it makes your hair smoother and thicker, reduces both existing split ends and the formation of new ones. I used to have hair which would split terribly. My last henna and my last haircut were over a year ago, and I still have NO split ends. None, nada, zip (although I do have a lot of brown outgrowth on top!). Henna also manages those flyaway frizzy hairs for good, with no need for lots of styling product.
But absolutely, positively, do not buy “henna hair dye”! Buy some body art quality henna - the kind used for mehendi - and use that on your hair. Those henna hair dye kits have low quality henna with twigs and sand and other additives which can do nasty things to your hair and scalp.
Check out www.hennaforhair.com and be inspired!
WhyNot, do you know if I could get the same benefits with an indigo/henna blend? I’m thinking of going a little darker than my reddish medium brown. I don’t think I want to go jet black again, but a dark dark brown would be cool.
Yeah, well I’m bored with your hair too, Queen Bruin.
So…sticks his tongue out…there!
I always figured everyone else was more bored of my hair than I am.
Oh shush. From what I remember, it’s just fine.
We’ll have none of your bellyaching around here…unless you brought that pie you were talking about…that’d be delightful.
Yep. Indigo isn’t as good for your hair as henna is, but it’s not as bad as the ammonia or metallic salts in “regular” hair dyes. If you scroll down on this page, you can find a rainbow of colors achieved with henna or indigo or some combination thereof. Click on a thumbnail to see a larger picture and usually a recipe.
Be careful who you deal with when buying indigo, though. There’re some unscrupulous people out there selling PPD, or Para-Phenylenediamine as “indigo” or more commonly as “black henna”. Besides being carcinogenic and mutagenic, it also chemically burns and irritates the skin in some people.
I know the woman who runs that site is reputable; I won’t vouch for other indigo sellers.
