If you aren't talented at figuring that out, then don't ask for dates in high stakes situations. Only ask in low stakes situations where a no isn't a big problem.

This means don't ask colleagues for a date. Instead, ask social acquaintances from other parts of your life.

Whether you are socially savvy or not, you should treat all business associates first and foremost as people looking to benefit professionally from their relationship with you. Treating women like their professional life is irrelevant because you find them hot is fundamentally not going to go good places. It tends to undermine them professionally. This isn't a way to "win friends and influence people."

It is truly scary the number of men in this thread who apparently do not understand what you're saying, as basic and obvious as it is.

When cultures go through radical changes, it is inevitable that some percentage of people will continue to operate under "the old rules" long after that has become problematic. If it isn't a problem for them in specific, they may honestly not realize it is A Problem.

Operating under the old rules is frequently not (apparently) problematic for well established people who belong to a privileged class. For purposes of this discussion, that would be men who make good money and see themselves as "catches" because of it -- edit: which describes a large number of HN commenters -- sometimes while being quite bitter about all the gold digging whores in the world and failing to see that if you bait your hook with money, you shouldn't be surprised if that is the type of fish you attract.

Additionally, some blind spots are genuinely rooted in personal disability. Lack of social savvy can be due to Autism Spectrum Disorder.

I have two sons who likely qualify as ASD. I find it very effective to give them helpful tools for navigating the social landscape and avoiding the worst errors they could make due to their personal handicaps. I find it quite counterproductive to blame them as if they are being troublesome on purpose.

I try to keep that in mind when framing comments of mine. I'm human and I don't always get it right by any stretch of the imagination. But that's where I'm generally coming from.