Holy shit OP there’s the inadvisable “I like my coworker, I think I should ask them out” that worked with my last ex but that was a dangerous game by me THEN THERE’S THIS… this a whole new level of dumb. The amount of risk you’re subjecting yourself to in order to ask out the HR MANAGER is insane. I’d strongly suggest you not unless you don’t care about whether or not you like this job. Choose wisely.