After looking at the feedback to date, whether received on my streamlined hypothetical or on the actual case itself that we’ve looked at over the last two days, there appears to be a few important points on which we might agree.

1) Co-workers versus industry acquaintances makes a difference when evaluating an after-hours opportunity; if it’s genuinely a team-building opportunity versus a highly casual confluence of persons in the same industry, many of us might be more likely to participate.

2) Potential for victimization exists, depending on previous experiences with persons of the opposite gender.  If an individual has had problems with persons of the opposite gender on a regular basis, one might do well to avoid after-hours informal situations weighted heavily to the other gender until one has worked through the issues.  This could mean something as simple as coaching from a mentor or more complex like therapy.

3) Trust your bullsh*t detector: if it “smells” bad, don’t do it.

Anything else you think I should add here?

What if it was your daughter in this situation?  How would you coach her?

In my opinion, I think the actual subject has issues with setting boundaries and could do with some regular coaching on this; until she acquired skills with setting firm boundaries, she should use the smell test and reduce her potential exposure until she felt more confident about the boundary process.  But that’s just me; learned this the hard way after working for a number of years in technology and in business.

Also think that the subject needs to have a few good and trustworthy male friends to consult on stuff like this, not just female friends.  Certainly doesn't hurt to have access to a broad spectrum of opinions!