I've said it before, an older man with zero dating experience may as well be on the sex offender registry according to many, probably most women.
Just an example of how ridiculous reddit can be, I asked this question to a Red Pill woman on the purple pill debate sub recently and got this response:
Date younger women in her early 20s who will be more forgiving.
This one is gold: Expect an inexperienced man to know how to get hookups, 'escalate' etc. with the ever-present fear of a sexual assault accusation hanging over things if he messes up.
Kind of like expecting a penguin to suddenly take flight and soar off into the clouds.