Tag Archives: pretty in pink

Hindsight Idols: Steff

30 Mar

Every style has an originator. A special someone who wears a look in such a way that everyone else wants to as well. Throughout the decades, teenagers have had their idols, and in many cases, tried their darndest to look just like them. Hindsight Idols is a section about the celebrities, characters and personas that we’ve wanted so badly to emulate.

This week’s Hindsight Idol is Steff, James Spader’s character from the 1986 film “Pretty In Pink”.

Feathered hair. White sport jacket. Collars popped. Shirt buttons undone. Aviator glasses. Loafers. No socks. As the yuppy bad boy, the character of Steff was the teen fashion equivalent to the Miami Vice look. If Sonny Crocket fathered an illegitimate love child with an ivy league beauty born into money, this is what he would look like. A little more subtle than the duds sported by Don Johnson, the Steff Look became the go-to dressy look for teenaged boys everywhere. Though it might not have been every day school attire, when the time came to attend Grandma’s birthday, a graduation dinner, or a Bar Mitzvah, out came the white suit and Sperry Top-Siders.

Sure, he was a bit of a jerk. A control freak. An ego maniac. A snob. But without Steff, there would have been no “Pretty in Pink”. What would Andie and Duckie and Blane have done without such a dashing antagonist? Happily gotten along? What kind of movie would that have been? The bottom line was that Steff’s general cuteness and bad boy arrogance made him impossible to hate. No matter how hard I tried, something about that tanned skin and blonde mane got me every time.

And so, Steff, The Hindsight Letters would like to salute you. Thank you for inspiring teenaged boys everywhere to pitch their socks and pop their collars. Andie might not have been your biggest fan, but we sure are. Besides, “that girl was, is, and always will be nada” anyway.


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Letter 42: Boy/Friends, Unicorns and Loch Ness Monsters

14 Mar

Dear me at 19:

You’ve just come home from a really tasty sushi dinner and a rockin’ concert by a Swedish Girl Band . You’re standing in your bathroom, staring in the mirror as you wipe away your mascara. You’re completely puzzled by the night’s events. You’re rehashing the evening, moment by moment in your mind, trying to figure out what the heck went so terribly wrong.

Allow me to clear something up for you: He likes you.

He doesn’t want to be your friend. He doesn’t want to be your “big brother”, even though that’s his self-proclaimed nickname and how he has positioned himself in your life thus far. He is into you. Big time. And, here’s a really big newsflash: To him, tonight was a capital D-A-T-E.

Looking back on the evening, I’m sure you must be piecing it together. He was wearing a dress shirt. His hair was different. He’d offered to pay the bill at the restaurant (though you declined). He made up a weird excuse for the two of you to go back to his apartment and asked to show you something in his bedroom (which you thought was super weird). And he lingered. Most importantly, he did a big time pout at the concert after you made a joke about your boyfriend (the one whom he knew you were dating). He’d stopped bopping his head. He was practically monosyllabic.

“What the heck is going on?” you might ask. “I thought we were friends.”

Let me fill you in on something here: The concept of the Boy/Friend is equally as fictional as the Unicorn, Loch Ness Monster and Santa. (Straight) Men and women simply cannot be friends. Sure, it might start out with the best of intentions, but sooner or later, someone decides to change the rules.

Whether anyone likes to admit it or not, there is always an unspoken sexual tension between (straight) men and women. Sure, we might try to act like high functioning, important and intelligent beings but ultimately humans are essentially a few chromosomes away from Chimpanzees. We are hardwired to procreate. The survival of our species depends on it. This makes it very difficult to forge meaningful friendships between members of the opposite sex. Because, no matter how hard we try to think of the opposite, we always just wind up thinking about sex.

Countless films, books and pieces of music have been written about exactly this narrative. Boy meets girl. Boy and girl become friends. Boy or girl falls in love. Tension ensues. Now, in the movies, this is almost always an excellent thing. Harry realizes that he loves Sally and they live happily ever after. What could be better than two friends falling in love?

Unfortunately, the real world is a lot messier. A lot of the time, the feeling isn’t mutual. And that’s the situation you are now in. You like your friend. You think he’s a great guy. You think he’d be a great boyfriend. But there just isn’t that indescribable spark on your end. That certain something special that makes you need him. And the fact that he feels that for you unfortunately doesn’t change anything.

Most unfortunately, this is where the road must end for you and your Boy/Friend. He is hurt. You are confused. And things are just going to get even more complicated. The best thing you can do is to tell him how you feel and allow him the space to quietly walk away, should he so choose.

Is it possible for a Man and a Woman to forge a meaningful friendship and keep it at just that? Maybe. Possibly. I mean, I’m sure that in the span of history, at some point, it might have happened. It could also theoretically be possible in the future. But in the meantime, I would suggest switching your hunt for the Boy/Friend to a mystical creature that’s a little less complicated.

At least at Loch Ness you might get a tan.


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The Hindsight Notes: Teenaged Bestie

3 Dec

Classic Teenaged Besties Andie and Duckie in the John Hughes Film, "Pretty in Pink"

The Hindsight Notes is a recurring section created for all you readers wanting to participate in THL, but lacking time to write a full letter. Each Note is composed of a question. All you need to do is answer it, in the form of a comment (below).

This week’s topic is: Your Teenaged Bestie.

Ever think about how much more intense your friendships were as a teenager? How seriously we all took the title BFF? How inseparable you were with your teenaged Bestie? There’s something about adolescence that bonds people in a way that doesn’t happen as you age.

So, tell us: Who was your teenaged Bestie? How did you meet? What was it that drew you to them? Are you still in touch? Now’s the time to share it all.

As always, I’ll start us out:



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