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I would be very careful and as others have advised, be sure your friend knows of your relationship with his girlfriend. Also, I would include him in some of the conversations you share via e-mail. He won't feel left out. NEVER EVER let her discuss their relationship with you. That will most definitely push things in a completely different direction. Walk the fine line carefully...
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Cruel words erode self-esteem like the ocean eats away the shore.
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