Asked 2 years ago
Maybe just the "suggest they try dating" bit -- your friend might be a bit upset with you if you tell the guy how she feels without her permission, since she gave you that information in confidence.
I doubt there's much to lose if they've been friends for so long, and if she thinks he feels the same way he might be going through the same things in his mind. Take the initiative and offer - the worst that can happen is a little momentary awkwardness.
and hope things can go back to normal if it doesn't work out
That is how me and my wife got together, a pushy friend smooshed us together
you can guage his reaction before getting to the dating part.
JFDI. guys can be shy.
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SHE should tell him, not you, unless it's her idea.
It's really easy when you're crushing on someone to exaggerate their reactions. Try to get independent corroboration.
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