Another problematic element of Riley’s behavior here is that he asked multiple times.
Conditional on asking out a colleague being otherwise acceptable, I submit that it is acceptable exactly once. The best potential argument against a broadly applicable no-asking norm—that it constitutes employer interference in the highly personal decisions of two people who may both want to pursue something—is significantly attenuated when Person B is already aware of Person A’s interest and can follow up if they change their mind.
An opt-in solution might be preferable here—such as a norm or policy against asking out colleagues with whom you have more-than-superficial contact at work [1] unless they have (e.g.) opted in on a third-party website (either generally or specifically with respect to you).
Another problematic element of Riley’s behavior here is that he asked multiple times.
Conditional on asking out a colleague being otherwise acceptable, I submit that it is acceptable exactly once. The best potential argument against a broadly applicable no-asking norm—that it constitutes employer interference in the highly personal decisions of two people who may both want to pursue something—is significantly attenuated when Person B is already aware of Person A’s interest and can follow up if they change their mind.
An opt-in solution might be preferable here—such as a norm or policy against asking out colleagues with whom you have more-than-superficial contact at work [1] unless they have (e.g.) opted in on a third-party website (either generally or specifically with respect to you).
I mean to exclude cases like: there are 1,000 employees and you may see this person across the cafeteria once or twice a month.