[snowwrestler]

Asking someone out on a date is not harassment, and it's fine if done maturely. Generally that means you take one, at most two shots and then if the other person turns you down, you drop it.

What's not ok is constantly commenting on a person's appearance or clothes, making sex-related jokes or comments in front of the person, staring at them constantly, questioning them about their love life or sex life, etc.

A lot of that stuff falls into the "harmless in a social situation" category, but is on the wrong side of the line for a professional environment. But, that is the sort of stuff that is often permitted, tolerated, or insufficiently discouraged by managers, especially folks who perceive work as a social setting, or want to believe it is a social setting.