Curious kitty cat, you need to respect the Big bad wolf's privacy.
Some people don't like to share. And people see that as being shallow or shy but its incorrect. Sharing too much information will make you weak, ever heard of the term "The loudest one in the room, is the weakest one"- Said by one of the Mafia lords which I forgot his name.
But for your case lets hope your guy friend is not an assassin, a seducer, or a male prostitute haha.
Ill use myself as an example. People ask me questions about dating and bar situations and I never share it. My friends perceive me as an attractive man that women throw themselves at, THEY ARE to an extent accurate, BUT although I know how dating works and the basics, sex was never a guarantee. and that is my reason for not sharing my dating experiences.
Same thing with my past military history. People are always curious to know what I did. and I never tell them because to me, its too traumatizing..
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Guys tend to open up a little more when they feel that that girl can be trusted. Girls rely heavily on emotions, so they tend to break secrets pretty easily. Guys are definitely more open with their male counterparts. If you want him to share information about his ex, he feels he needs to trust you, and if you want him to achieve that fast, you should place some trust on him and maybe open up a little bit to him so he knows that you trust him.
On a side-note, depending on how you have revealed secrets that other people trusted you with. If you have talked about other peoples secrets accidentally with him, as a guy, I will keep that in memory and tend to not be as open with you.
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Do you think it's good when people go around telling other people what you confided in them? Could you trust them with your secrets if they did? Would you feel comfortable sharing your vulnerabilities with someone that would go and tell it to whoever? It's call loyalty. It's call respect... When guys form bonds with people what happens between us and those people is between us, we don't go gossiping about hem behind their backs, and we don't like girls that do that either. The more a girl gossips, the less I will open up to her... You don't sound trustworthy enough to guard anyone's secrets, so no one is going to tell you jack.
Girls like a bit of mystery. Guys who cultivate an air of mystery, are more appealing to the opposite gender.
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