Hmmm.. I have a slightly different take on it. Yes, I agree you need to respect his wishes to let him do as he pleases.

However, at the same time, you could point out to him that you disagree with his therapist's advice, that you'd hate to see him get hurt again, that you're only looking out for his best interests, but that ultimately it's up to him to decide what to do and you won't interfere. That you simply are expressing your care and concerns that he has already been dumped twice by the first woman and (most likely) will be again.

Good friends don't just always agree & go along with ALL of their friends' actions. A good friend will be honest, even if it pisses off the person. A good friend is true to their own feelings & opinions about what their friends are doing that is harmful. Like, if a friend were an addict, would you stand by and allow it and enable them and encourage them? Or would you say something that their behavior is harmful?

The thing is, he probably WILL get rejected and/or dumped again by the first woman. Both women have dumped him, so what he really needs to do is explore the reasons why with his therapist. And I agree that his therapist is giving really bad advice. Why she is saying he should explore his feelings, despite being dumped twice, is beyond me.

But if he chooses to walk down this path, it's his choice and his own doing. He is walking into flames of fire again -- OUCH.

It's SO hard to watch a good friend hurt themselves again and again, I know. It's painful to witness and to stand back and allow it to happen. But perhaps he needs to learn on his own and through painful rejection that going back again and again is not wise. He hasn't learned this yet.