My wife and I really like this man (lets call him Bill), he used to live next door to us. He and his wife divorced about 18 months back; it appears as though she has moved on. She still lives next door to us and so we have noticed that each weekend the boyfriend stays at her house.
I suspect that she is hiding the boyfriend from Bill. I also suspect that the reason for this is that Bill is providing some financial support for her. While this is purely speculation there is some evidence that supports these suspicions.
In relation to Bill, he seems unable/unwilling to move on. For example last night he posted on Facebook that he is very much still in love with his ex-wife.
The interpersonal problem:
My wife and I are leaning towards telling him about the boyfriend, as we feel it will help him move forward.
So the question is: In what way would we broach this topic? Bearing in mind both the situational context, and his current emotional attachments.
The goal is to avoid causing him any more pain than is necessary in delivering this news.
Update: I went out with the friend with the goal of supporting him in life, he is just a good guy. We rode bikes and stopped at a pub had lunch and a few beers. At one point he broke down crying, but not for long. We talked a lot about the only thing that he can control: his actions. This probably went on for about two hours.
Our discussion turned to he suspected that she was seeing someone else, and all I did was confirm it. The way it went down he was relieved to know and being that my main goal for the day was to support him it was well received. Hopefully this help him moves on. He suspected that she was going to end up with a doctor or something, but that is not the case, the guy she is seeing is unable to afford his own car.