What would you do?

A friend of mine - we’ll call her Debbie - called me with a moral conundrum she is facing.  It would seem that another friend of ours - we’ll call her Sally - is dating again, and the moral and ethical behavior of this particular gentleman seems to be an issue for Debbie.  First, a little background:Debbie, Sally and I have known each other since kindergarten.  We went all through school together, including university.  As if that weren’t enough, we also ended up teaching together within the same school division, Debbie and Sally at the elementary school and I at the high school.  Debbie always knew she was a lesbian and I always knew that I liked boys.  Sally, ever the free spirit, had several relationships with various men until she met the man she thought would be her life partner.  But, as luck would have it, he turned out to be less than reliable and left Sally - and their two young daughters - after ten (what Sally assumed were “happy”) years.  Being a free spirit, Sally felt no need to marry this gentleman, and to her credit, did not stand in his way when he announced that he was leaving her for another woman.  To his credit, he still maintains contact with his daughters and provides for them in every way.  So, you might be asking, where is the conundrum?About a year ago, Sally began dating a teacher from the high school.  I know this particular gentleman and taught with him for all of the years I was at the high school, although he and I were never friends.  He always struck me as relatively open-minded and my dealings with him were always of the professional variety, with the occasional chat at the photocopier in the morning thrown in for good measure.  Sally, being the free spirit that she is, embraced this new relationship with her usual “Let’s see what happens” attitude.  Fair enough.Debbie, not being a free spirit in any way shape or form, was suspicious of this new romance.  It would seem that Debbie’s suspicions were well-founded because, as she explained the situation to me, Sally confided in her that she’d received an anonymous email from someone warning her that this new gentleman was “not to be trusted”.  The email also provided some very concrete (some of it photographic) proof about how this gentlemen seemed to be involved in every imaginable “scene” from woman to men to groups to kink.  While Debbie was taking this warning rather seriously, it would seem that Sally felt inclined to disregard the warning as “frivolous” and “from some jealous bimbo”.  Fair enough.I have always made it a policy, when friends ask for advice, to turn into Lucy (of the Charlie Brown comics) and become a quasi-psychiatrist-type friend and turn the questions back on them.  So when both Debbie and Sally asked me one evening on the phone, “Would you give any credence to this anonymous email?”, I asked both of them whether that was the central issue.  Instead, I asked Sally whether she felt she needed to show this email to the gentleman himself.  Is he actually involved in all of those scenes?  And if so, is this something he plans on continuing while in a relationship with a woman who has two young, impressionable children?  In other words, will he be truthful about his intentions?  (Honestly, if the man is a player, I don’t think Sally would really care; she’d chalk it up to experience and a fun time and move on.  I have no doubt that Sally would not allow such a man to have any kind of role in her children’s lives.  But if those days of fun and adventure are behind him and he is looking for a family, doesn’t he deserve the chance to prove it?)“As far as I can tell,” I explained, “it would seem that the real issue here is whether you can trust this man around your children.  Your children are both very young and impressionable and if this man becomes a part of their lives, can you ALWAYS trust him to do what’s in their best interest.”  Sally admitted that I had a point, but expressed her usual frustration that I did not actually answer the question.In all honesty, I had to admit to both Debbie and Sally that I didn’t know what to think of the email or how I would actually feel faced with a similar situation.  Personally, I’ve always been the type of person to rely on my gut; if the man I’m interested in is less-than-truthful or if I catch him in a lie, it’s over for me.  Perhaps I’m just a hard marker, but experience has taught me that if a man will lie about one thing - however trivial - he will lie about anything.So, my question now is this:  “Faced with a similar situation, would you give any credence to this anonymous email?  Is it a vindictive strike of revenge or is it a prophecy of heartbreak to come?"