Probably when I found out something about 95% of the girls I've met involving taste in men and preferred role/type of sex.
It was shattering to me, and the hopeless romantic in me was shocked, horrified, and then it killed itself.
And slowly, but surely, as I changed myself to be attractive to the ladies, my uniqueness and creativity have slowed, and I look at relationships (including my own) with jaded eyes, and hope for and expect nothing, so when some inevitable good happens, I can be happy for about 20 seconds before I realize none of it really matters anyway.
Yeah.