Ok so first off thats not how that usually goes. Straight men do not typically find the male form attractive at all, so we always think an attractive woman looks MUCH better than us, even if they think we are hot af, simply because we aren't the gender we find attractive.
This doesn't result in insecurity though, nor does envy of lifestyle, similar to how when you find a really cool thing at the store that you want, you aren't comparing yourself to the thing, you are simply seeing it as a prize to obtain, a treasure.
To men, women and prefered lifestyles are a luxury, a need, and a friend, not a form of competition or something to compare ourselves to, we do not view the perfect woman as "superior" to us, we view her as what we get if we don't settle, same goes for lavish lifestyles.
That said, most men are still afraid to approach women, because women are mean af if they don't like you, doing everything from labeling him a creep, to ruining his life, all just because he thought you were pretty.
Too many women are ruthless jerks, so men should never approach women, and should always wait for the woman to approach.
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I was in that situation, but I didn't feel awkward. But I was a "shy guy" because I never had a girlfriend before. We became a couple because she made the move.
She's a rich lawyer now.
I shovel shit made by my wife's horse.
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