Dear Frustrated,

Your theory, Frustrated, is basically right. He won't move on if he is always seeing her and clinging on to the faint hope that she'll go back to him.

The thing is, that's much easier said than done. And it should not be done by you. This is something that has to be accomplished by him.

Don't Contact Him Yourself

You cannot tell him "don't go near my girlfriend, it's for your own good." He won't buy it and it will only serve to, in his mind, lionize him while demonizing you. He may start to hate you and an obsessive hatred of you is just as unhealthy as obsessive love for Jane.

It's All About What's In His Mind

He has to want to heal and get over her. And in his own mind it has to become clear that he won't get her back.

Only when he accepts this will he want to make the recovery.

I agree. This isn't his decision.

But neither you nor I are able to make this happen.

She Should End The Friendship

I don't think she really wants to. She likes all the attention.

As for Jane, she may be the only one to have the power to change things. She is right to want to stay friends with him and that is nice, but as you said it isn't going to help.

The more time he spends with her and the more friendly they get the more likely he is to believe that he has a chance to get her back. Once he gets shot down again it'll double his hurt.

Another Woman Could Distract Him

The only other person who can change things is another woman. If his attention can be diverted it may give him something else to concentrate on. I don't suggest you go and try some sitcom inspired scheme to set him up, though. I've seen a lot of TV and it's never a good idea.

– Buddy