A colleague and I were yammering about those cringe-worthy blackmail photos your friends from grade school put up on Facebook (see one of mine, age 11ish, above). We concluded that such an awkward, gawky, face-for-radio phase of life is good for a kid to go through, because it forces you to develop skills other than acting cutesy to get what you want, and (if you’ve got a minimum of empathy) teaches you to have compassion for others, even when you’ve emerged, somewhat more swan-like, in a year or two.

(My experience as a dork taught me to have compassion for Yasmine Bleeth, with whom I went to grade school, because she never had a discernible freakish period. Right now, considering what a riot it is to post these pictures, she’s probably feeling terribly left out. Which is tragic.)

In any event, check out my body language in that picture. I am descending that staircase as if I am Miss Pre-pubescent America about to accept my tiara and my Grand Prize: a chance to go roller skating and share a strawberry shake with Shawn Cassidy (two straws!) Self-esteem, even though I was at my absolute least attractive (please take special note of my brown tinted prescription glasses, which had my initials in the lower corner of the right lens) was clearly not in short supply. I thought I was the SHIT, appearance notwithstanding.

It was only later, when I looked much better–thus the “hot” in  Formerly Hot–that my self-esteem was in the sub-basement. It wasn’t a consistently inverse relationship (i.e., It wasn’t as if, the better I looked, the worse I felt) but I felt pretty darn awful about myself for a good deal of my teens and 20s, when many people were paying lots of money to get their hair and their boobs to resemble mine.

Finally, in my 30s, I managed to look good and feel good at the same time, most of the time.

And now, of course, I feel great, just as the first signs of decrepitude are surfacing (who even knew there was a such thing as nasal labial folds until OMG there they are! And as deep as irrigation ditches). I am reasonably sure my self-esteem will continue riding high, unless I screw up mightily.

So clearly the relationship between the way you look at how good you feel about yourself–even if, like me, you’re a bit preoccupied with appearance and work in media and live in New York where people pay way to much attention to that kind of thing in general– is not clear cut.

Why, then, do we always hear about people getting “life-changing” plastic surgery or going on diets that profoundly affect their self-esteem? I certainly understand the achievement aspect of losing weight–it’s freakin’ hard–as well as getting positive feedback from others about how you look making you feel good. It’s hard not to internalize that, and why shouldn’t you? Take what you can get. But clearly looking good is not to be relied upon to boost self-esteem (just think of all the suicidal, anorexic, miserable, drug-taking models out there). And if you can’t rely on it, to keep it tucked away under your mattress to use when you are running low, what they hell good is it?

Thoughts? When in your life did you feel best about yourself–like you rocked and you could do anything–and did you look your best at the time?  Please comment below.

Photo courtesy of Diana Hollander