Lately humanity has been on an upward trend of becoming less accepting of adults having sexual contact with the underaged. We don't know for certain that Kirk's mom was what we'd consider underaged. Maybe you wait until you're 22 in the future to get educated about Love. But it doesn't sound like it. And "James" was just the first love instructor.
As far as other worldbuilding he did.. well what? having a brain implant to get secret messages beamed to you? Seems plausible but also something the Federation tends to be wary about.
But back to love instructors. Let's see what the Great Galactic Bird had to say about such things: