How do I win a playboy's heart?

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A playboy is one of two things.

Either he is a person with a giant hole in his heart that drives him to try to fill it with empty intimacy and affection, empty because he is unable to return it.

Or he is someone you think manifests those personality traits because of a cursory look at the surface elements that he presents. Guys don’t just hide their bad traits from potential mates, they also hide good ones.

It’s important to know which animal you’re dealing with because it’s going to make a real, serious difference in how you interact with him.

If it’s the first then the right approach involves you playing the role of therapist.

If it’s the second then the right approach is to just treat it like a normal relationship.

If you think he’s emotionally healthy and he’s actually damaged and you treat it like a normal relationship out of perfectly-normal human altruistic instincts, then he’s going to use you to try to fill an unfillable hole in his heart and when he finds out that you’re not going to fit in that hole, he’ll throw you away and find someone new. Your goal of winning his heart will feel true, right up until it’s not anymore.

A therapist’s job is to act as a mirror on the patient’s behavior so the patient can eventually see where and how he’s going wrong. It’s hard work and can make you feel like you’re babysitting a two year old. But it’s necessary because the other person simply cannot maintain an emotionally healthy relationship. Any path from a unhealthy relationship with someone with a hole in their heart to a healthy one has to travel through the process of catharsis.

The converse isn’t nearly as hard to deal with. Basically if you approach someone with the mindset for therapy and they’re just interested in a normal relationship, then they’re going to struggle to find meaning in that relationship. Because you’re not really dealing with them, you’re dealing with the illusion you have of them. Not nearly as bad as if there’s actual trauma involved, but not as bad as an abusive relationship..