The premise of this movie is just a big cultural face palm.
Not really. I've dated way younger and it is uncomfortable. And that gap will always be there. Now over time the gap is less and less of a big deal, but it's the biggest deal at the beginning when the relationship is its most fragile.
I got the feeling he realized it wasn't going to work out long term and didn't want to get hurt (acting like he was protecting her..but he was really protecting himself).

For a guy in his 40s, it's incredibly silly to me that it would be a problem for anyone that a 35-year-old guy dates a twenty-something.
Yes, I feel like I'm too old for that type of relationship. But the difference between the 20s and 30s is really not enough to possibly view that relationship as a moral or ethical issue.
The premise of this movie is just a big cultural face palm.

I kind of got the feeling that he knew they weren't going to be together long term (probably her changing her mind a few months or a year down the road) and he didn't want to set himself up for that.
I don't think he settled for the bookstore girl. She was very cute and close to his age. If that is "settling" count me in! Also, we don't know much about their relationship so it's hard to say that he's settling when we only know they ended up together. Now how they truly are together.

He was being immature, although the film is about growing mature ('no one is really an adult, it's the world's dirty secret' - line from the film). His was the typical reaction of a self-conscious, bookish snob: mind over heart, or imagination over reality. If he loved the girl he would have loved her physically, too. Unless he thought of himself as her mentor and pal, which he did. It's called emotional immaturity, no matter how many theories he manages to pile up.
Then apparently he settled down and got real with the bookstore girl, but where's the spark and the spirit? So he made a compromise, which for most people means growing up (not that they are right about that).
We can't be lost; we don't know where we're going.
All that matters is that we're going.

I asked you this and you didn't respond
If you are in a happy relationship then why are you mad at someone for not screwing someone he had no long term future with?

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Anyone who disagrees with you is a troll.
Cool. Got it.
I'm going to let you have the last word since you clearly need it more.

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If you are in a happy relationship then why are you mad at someone for not screwing someone he had no long term future with?

You couldn't answer what's interesting about this film, but apparently you are an expert on the subject of Sex. What are you, Dr. Ruth?
Ooooh, big scary "taking advantage of", which wasn't even the case anyways. They're both adults. If he wants to let fear and naivete get the best of him, it's his loss. He, like the film, should be more dimensional at this stage in life, instead of hiding behind book pages and theory. She helped him out of his shell apparently, it was about time.
Oh yeah.. and how convenient that the bookstore girl is a) attractive, b) available c) his age d) finds him remotely interesting.
By the way, I myself am in a happy, meaningful relationship with a smart, beautiful woman. So no, wrong again. Not that it's any of your business.

He chickened out on being intimate with someone he obviously really liked, thought about, and had chemistry with, don't tell me he wasn't attracted to her.
He had a feeling that it wouldn't have worked out and he didn't want to take advantage of her.
He fumbled the ball away inches from the goal line because of some morality nonsense that he quickly ends up contradicting by shagging his former, older Instructor.
He was fine nailing the teacher b/c she was old and no one was being taken advantage of.
The letters back and forth were more cringe-worthy than a hallmark card. Oh sorry, were you clutching your heart during that part?
Why do I get the feeling that you are single? (this is where you tell me that you are dating a model and you are a black belt in everything). It's the internet, go big!
I didn't even want to watch this movie b/c Josh Radnor was in it and I ended up really enjoying the film. I don't think you are wrong for disliking the film. But I do think you have a warped view about sex. It's okay to say no every once in a while. Maybe you get it so infrequently that you don't want to waste your limited opportunities?

What else exactly was I supposed to be so enlightened by?
It was already a strain to find this clueless bookworm character interesting enough to deserve his amount of screen time, but we had no choice since he wrote the script. He chickened out on being intimate with someone he obviously really liked, thought about, and had chemistry with, don't tell me he wasn't attracted to her. He fumbled the ball away inches from the goal line because of some morality nonsense that he quickly ends up contradicting by shagging his former, older Instructor.
The letters back and forth were more cringe-worthy than a hallmark card. Oh sorry, were you clutching your heart during that part?
And even if he was "right" about the Vampire books (Twilight inspired obviously) being crap, he was a pretentious ass about how tactlessly he handled discussing it.
Clueless. Can't root for that.

Is that all you took away from the film?
Your life sounds joyless.