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In that case, it's probably important to let him work through it himself.... and he will.
She told you right out she didn't want to sleep alone. Listen to what she's saying. We men don't listen always. Stop thinking about it so much. I bet you haven't slept again since then or have you. Take advantage of the moment. A lot of what you have described is going on behind close doors. I had opportunity to did this once and I was asked not to leave. So I had stayed and was lead to her bed and that started the relationship from then to 2017 that has ended. On the bright side I met a woman from work and everything working out she's here with me so far 1 week after her family issues where solved. I paid for her flight here to be with me. Everyday we drive to work in the same vehicle. Just feel so different to me. Sleep in the same bed and have fun.. That's what life is all about having fun. If this woman is interested in you, then go for it. Don't rush or push it let it happen my friend.