[throwanem]

You don't need to see an agenda behind every invitation to recognize the agenda behind this one.

For those genuinely unclear, it's a combination of things - the individual nature of the invitation, the private nature of the venue, the timing and explicit involvement of libations whose effects often include the lowering of inhibitions - all in all it's just a super sketchy thing to all of a sudden pop up in a previously professional relationship. Any one of those would be fine; any two would be a little questionable but probably okay; all three at once constitute a great big flashing neon sign that spells out "YOUR BOSS IS TRYING TO LAY YOU".

[vidarh]

And if said boss isn't trying anything, he still ought to understand the signals it sends sufficiently well to either 1) not do it, 2) invite more people (and make that clear in the e-mail), or 3) make it something much more casual than drinks on a Saturday night.

If he doesn't understand that, he'll be the kind of manager that creates liabilities by leaving e-mail trails of questionable invitations that might get caught up in discovery if/when something happens.

[webkike]

I mean that's the thing, I don't deny that if this a purely professional relationship then this comment is incredibly out of place. But often times professional relationships become less professional and more friendly. I don't deny that it is creepy from your perspective.

[throwanem]

I mean sure, but if that's the nature of the relationship, nobody's going to be made uncomfortable by the invitation - that's probably why the context in which it was mentioned makes clear that's not the case in this hypothetical. My comments are addressed more toward the "what could possibly be wrong with that?" kind of response it seems to have elicited, and intend to supply that question an answer.

[webkike]

I see