hair conundrum

[i love that word - conundrum, fun to say!]

i got my hair cut on monday, i'm still sporting the soccer-mom-bob, although i don't think of it that way. i'm chic & stylish (remember i buy outfits at walmart? hmpf, maybe not so much...)
the bangs are growing out, so they are sideswept & the bob is about chin-length.

for the 3rd time the stylist has asked me "what are we going to do about color?"
now to some degree i realize it's a stylist's job to beautify (& make money) but i'm kinda stuck. i've been highlight my dark-brown hair forever, really since my teen years. when i was a kid my hair would lighten with the sun but by the time hormones started kicking in, my hair darkened so much mere sunlight wasn't powerful enough.

the only time i didn't highlight my hair was when i was pregnant & i didn't like the way my dark hair looked on me. now though i'm worried i'm one of those people, ok women, that doesn't change their look, ever, like i'll be 60 years old & still doing this, hanging on to that look that worked many, many years ago & not so much anymore. i might as well sport a bee-hive updo & heavy black eyeliner a la amy winehouse..it works for her right?

so i don't know if i should highlight the new growth or should i color it all something similar to my natural color & let it all grow out.
i guess part of this is in october (yes i realize in certain ways that's far away but in hair growth it isn't!) yeah, october, it's my 20 year high school reunion & i don't want to look like i'm trying to look like i'm still in high school.

oh yeah, & facebook has finally located a few good friends after being such an ass (remember strike #1, #2 & of course we can't forget #2.5).