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Sex, innocence, and naivete. TL;DR: WHY THERE'S NOTHING CUTESY ABOUT BEING A VIRGIN.
Firstly, I think it's relevant to define the difference between naivette and innocence, as far as Steve is concerned. He was born on the brink of the Roaring Twenties; he came of age during perhaps the single bloodiest period on America's home soil outside of the Civil War. When he was young, the fronteir of the risque feminine became short skirts and big guns; popular sexualization of the feminine was as prevalent then as it is now, though by today's standards it might be considered demure. Today's standards aren't exactly anything to brag about.
He's about as far from naive as you can get, if we're being perfectly honest. He's lived in the slums during the Depression, inevitably seen the worst humanity has to offer in terms of selfishness, violence, and indifference. It's one of the things that makes his determined humanism so remarkable; logically, we expect exposure to that kind of behavior to result in more of the same. It's no suprise that he comes off as guileless and naive, given the expectations of both his surroundings and our 'modern' perspective.
He's not.
What he is, is shy. Inexperienced, certainly. Before Project: Rebirth he'd never had a girl look twice at him except as a pity project. That hardly means he doesn't know what beauty is, what a naked woman looks like, or that he doesn't feel sexual attraction or know what one does with that attraction when both parties are interested. Both parties being the issue in this case.
He was raised by a single mother who probably got shunned for being pregnant and alone, regardless of the fact that her husband had died overseas; the importance of respecting women and their bodies and feelings probably got drilled into his head with the force of a psychotherapist lobotomizing a problem patient. That, combined with feminine lack of interest and his primary sources for romantic propriety being film and - well, Bucky, combined with the fact that he's smart enough to know it doesn't work like in the movies, combined with the fact that he's too intense and committed a person to just want a one-time fling, resulted in one twenty-six-year-old virgin who's gotten comfortable with being that way. As he tells Peggy, inviting women to dance always seemed terrifying - and then, it just didn't matter that much. He's happy with the person he is, the man he is, and doesn't need sex as a validation of his masculinity.
Even before the project he had that resolution; after, when interested women were suddenly in plentiful supply, he kept himself to himself. Part of it is the assumption that any woman showing an interest is either going to make fun or him or treat him like a child. Part of it is the fact that he honestly, truly doesn't think about sex that much. It's not the most important thing to him when it comes to a relationship. He wants someone- needs someone, really -who is as intense and dedicated to something as he is. And that kind of person isn't going to think about sex first and foremost, either. Attraction for him isn't simply physical. He knows from experience how unimportant phsyicality is when it comes to a person's true nature; personality is what he falls in love with. Integrity, resolve, bravery, intensity, commitment. The connections he makes run much deeper than those that first-blush sexual attraction provide.
As such, when it comes to actual physical contact, a little goes a long way in his mind. A gentle touch, a long look, a close brush when passing each other. To 'be with' someone means just that - to be with them. There's no shame in chastity. In Peggy's case, there's honor in professionalism and respect for her boundaries. She worked hard to get where she is, and nothing would undermine it faster than being caught kissing in the stacks, figuratively speaking. She's fought too hard to be seen as a soldier and agent of resistence first, regardless of gender.
It's easy to assume that because he's a virgin he's also sexually naive. But again, innocence, reserve, and naivette are not at all the same thing. Just because he doesn't insist on sex doesn't mean he doesn't know about it, or that he's not aware of the kinks that exist out there - I mean come on. His best friend is Bucky "Well Hello There" Barnes. Steve is uncertain, nervous, shy. But most importantly, he chooses companionship over physicality, and I have more respect for that than for any guy who keeps a score card under his pillow.