Hi Matt –

I think it’s possible that you are too close to the situation and not looking at it as wholly as you could be. Indulge me for a moment with what I see as the situation; your now girlfriend engaged in an affair with an old friend who was in a relationship because she was lonely and he was not in a great place mentally. The affair progressed to the point where the old friend wanted to change his relationship status to include your girlfriend (while presumably getting rid of the other girl, but who knows if he wanted them both?).

You spend a lot of time talking about how his mental space affects your girlfriend, but the obvious question to me is: Why did your girlfriend think it’s ok to have an affair with a dude in a relationship because she was lonely?! You may have an answer to this question, or you might not have asked it yet, but in either event I would spend waaaaaay less time focusing on this old friend and more time focusing on the actions of someone who is now included in your life in a very intimate way. I realize love makes us assume the best in people, and it’s very difficult to differentiate between what someone does and how they make us feel. But brother I gotta be honest and say that the mere fact that your now girlfriend was involved in that situation at all is a result of her actions and her reasoning process. She clearly at some point thought what she was doing was fine – and/or justified it in some way, shape or form to herself. She was a willing participant in a lie that (sounds like) destroyed a relationship (either in part or in full) and contributed to bringing two people down low so she could feel better about herself. Now I don’t know this girl, nor do I need to really – this might sound harsh, but this is also a 100% honest, first-impression reaction to your story.

Bottom line – don’t worry about the friend, spend more time talking to your girlfriend about how she conducted herself and how she co-created the situation she now finds herself in.

My 100% honest advice – dump her, cheaters don’t change in my experience. Life’s too short to deal with someone who cannot control themselves.

All the best,

Mike