> Please be careful though to not brand people as immoral simply because their past is different than yours.
> From my perspective, I do not find a strong correlation between "sexual history" and "morality".
I doubt that your definition of “niceness” is right. Morals (to me at least) is the basic rules that you live your life by – so it is inherently a personal concept.
So whatever morals you live by – he may live by a different set of morals and feel that excessive intercourse may be immoral. There is no reason for you to blankly dismiss his moral values (just because your personal morals are not the same as his). Whether you agree with his morals or not – the fact remains that it is real to him and he chose to live his life by them.
> Bringing up the topic of sexual history with a woman is generally a huge turnoff.
In every relationship you must discuss several things that may or may not be a turn-off (e.g. religion, politics, views on certain things such as abortion – basically everything that we do not discuss on HN). This may not be always pleasant – but it still is important.
> When you do so, you are clearly judging her and telling her she must fit some predetermined notion of what you, a man, thinks a woman's place is in the world.
No. It is important to discuss all of those things in a serious relationship. If you have a notion of a girl that differs from reality it is important that you know that. If the relationship ends because your notion of her is different than reality then it is ultimately a good thing.
If you have ever been in a relationship and your partner did or said something and you thought “WTF??” you will know this to be important.
> My only training on this matter is from living my own life and having to grow out of some of these issues myself. To put is bluntly, this is the common story of the geek who didn't get laid in high school and has evolved a blanket of morality around the reasons why.
Maybe. My take on this is as follows (I am not a US citizen): The USA became sexually liberal extremely quickly – and even now there is huge encouragement from media to engage in casual sexual intercourse (+). IMHO I don't think that this is the right approach – and sexual intercourse should preferably go hand in hand with stable monogamous relationships.
I don't know what this USA view is that you 'have to get laid' in high school and that it is a shame to be a virgin. It is stupid (Paris Hilton stupid).
Even if the past was too conservative, I think the pendulum swung to much to the liberal side – and the good position is somewhere in the middle.
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(+) If I sound like your father/grandfather forgive me – it was not the intent.