Thank you for writing to Alterheros!
First I suggest you take some time to evaluate what your comfort zone is: ask yourself how much of a secret you want to keep your sexual orientation. If you are certain that you want to keep it a secret, then I suggest you find a way to ask him without telling him about your orientation. Here are some options you could consider: maybe try to find out through his friends, or if you prefer talking to him directly, you could bring up the subject by discussing tastes in movies, and in actors, and then maybe ask him what he thinks of particular male actors. Or you could tell him about a book you read that has homosexual characters in itc you could also ask his opinion about topics like gay marriage. Essentially, these are indirect ways to get to know him better, and maybe learn about his sexual orientation. It does not all have to be within a single conversation, you could bring up the topic a couple of times before you ask him about his personal tastes. If he seems uncomfortable, it might mean that these are things he prefers to keep to himself. However, you will have established trust during those conversations, so maybe after some time he will open up to you.
On the other hand, if you do not mind telling him about your sexual orientation, and you think you can trust him to keep the secret, then I think it might be easier for him to open up about his own sexual orientation after you tell him about yours. Is he a real friend? Do you think he will judge you? Be careful if you do not know him very well yet, because there is a possibility you might get hurt: sometimes people react defensively when you ask them personal questions. And whatever his reaction is, you can always ask him to keep this conversation between you two.
Good luck, do not hesitate to send us more questions,
Julie, for Alterheros