Actually nothing has made me feel older than being "the mom" in the eyes of the babysitter. How did that happen? It seems like I was just the adolescent riding in the car trying to make conversation with the mom. And now I'm the mom, trying to make conversation with the babysitter. I think that I feel as awkward now on my side of the conversation as I did 20 years ago on the side of the babysitter.
Honestly I was never cool. No one in high school would ever have called me cool, and I didn't even want to be "cool." In fact, I thought that people who spared no expense of time or effort to be cool had a "cool complex" that didn't ring true with me. I wanted to be liked, yes, and respected, but I honestly spent no time worrying about being cool. I do have to admit, though, that it delighted me when a friend of mine in junior high told me she thought that I was cool in 5th grade, because I wore yo-yos (those big platform type shoes that are now sort of back in style! I think that they were my mom's, and I don't think I wore them often).
But what is cool? Does it exist beyond the social structure of school? If cool means feeling pretty good about who you are, then I'm pretty cool at 35. I think that cool doesn't exist in a vacuum. There's some sort of evaluation from others required. I think the best we can hope for now is to fall into some sort of cool category.
Cool Mom--a mom who knows when to keep her mouth closed (most of the time if there are others around); dresses fashionably, but not like a teenager herself; a mom with not too many rules
Cool Friend--this just means you are cooler than the friend calling you cool, either because you have cool Mom status, better clothes, or hipper taste (in clothes, music etc).
Cool Aunt--a variation on cool Mom. Aunts are cooler than mom by definition. A cool aunt is allowed to dress like a teenager and still be cool. An aunt can give the same advice as a mom would, but it comes off cooler.
Cool Grandma--looks or acts younger than her age; comes with perks, such as buying ice cream without worrying about spoiling dinner, doing special crafts or activities on request, and saying "yes" more than "no"
Dictionary.com didn't even really have a satisfactory defination. In the slang category, "excellent or first-rate" as in a "cool sports car" is as close as it comes to my mind's eye view of the word.
With that in mind, here's my definition of a cool (excellent and first class) person:
fun to be around
presents him/herself outwardly in a pleasing way, even if she isn't traditionally attractive
puts the needs of others ahead of her own
no offputting social habits, such as drinking to excess or using foul language