I think it’s obviously inappropriate to ask someone out at a work retreat (and obviously inappropriate for people to date people in their chain of command, etc.). But I don’t think that colleagues asking each other out is always unprofessional, if they know each other outside of work and if a “no” is respected. For a reducto ad absurdam, Google employees don’t have to avoid dating all 180,000 other Google employees. Clearly, in a smaller organization, asking people out is more fraught and often wise to avoid. But I don’t think it’s wrong 100% of the time. I have dated work colleagues before without a problem.
(TBC I don’t mean to defend Riley’s behavior here, which clearly crosses a line.)
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 think it’s obviously inappropriate to ask someone out at a work retreat (and obviously inappropriate for people to date people in their chain of command, etc.). But I don’t think that colleagues asking each other out is always unprofessional, if they know each other outside of work and if a “no” is respected. For a reducto ad absurdam, Google employees don’t have to avoid dating all 180,000 other Google employees. Clearly, in a smaller organization, asking people out is more fraught and often wise to avoid. But I don’t think it’s wrong 100% of the time. I have dated work colleagues before without a problem.
(TBC I don’t mean to defend Riley’s behavior here, which clearly crosses a line.)
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.