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The warning sign here are the times he has to talk to her when he is with you guys. This is a sign of insecurity on either his or her part. Note that I'm not blaming her here. Many times the guy is perceiving he needs to call rather than needing to call. There may be no hope here. If she is the one that is insecure and mandating that he call, then all you can do is hope he sees the light eventually. If it is he that is insecure, hopefully he grows out of it.
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