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We can talk logically about how people should react to this or we can talk emotionally. I think the latter ismore important here.
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This is exactly what I was going to say.
There is a tendency in life, and especially on the forums, for people to act a bit too coldly and rationally when dealing with other people. And assuredly, the rational way is the right way. But, of course, this is a very sensitive issue for your friend. He obviously knows that the rational thing to do is to 'not care', but he still does, somehow. That's because he's human and privy to emotions.
If I were you, I'd go ahead (after all, there is nothing wrong) but be very, very sensitive. Make only the smallest remarks to the friend about her, and make sure to spend time with him - if you were seeing him three times a week, don't start waiting for once a month. It'll be completely unjustified.
Jam it back in, in the dark.