This is one of those major life dilemmas that serves as a test of character. To date or not to date the woman, that is the question. Perhaps I have the answer you woman women. The goal of course, is to have it all, The loyalty, respect and love of your buddy, but also a relationship, sexual and otherwise, with his woman. You want to keep him around as your ace in the hole, but court and date her too. Is it possible to have your cake and eat it too? Perhaps. Sometimes it depends on your friend though. Some women are apathetic about their women and seem not to care who dates them at all, be they friend, enemy or anyone else for that matter. Then you have the Romeo and Juliet or West Side Story scenario, which can result in a major turf war and in the end, life. Sure, this is the very extreme result of illicit love, but hey, it happens in some circles. Just ask the Capulets or the Sharks. If you want my opinion, however, and I assume you do, the way to approach this very delicate matter is with prudence and respect. Never assume that just because a friend treats his woman with contempt that you can step in and take her out to dinner. When push comes to woman women, as it may very well in a situation like this, most guys will have a word or two to say about you and their woman. You know what I mean, right? The talk. The one where you sit him down and confess your attraction to his woman and iterate your honorable, I hope intentions. Do not make a move her way until you complete this crucial step. He may spend more time with you and you may know more about him than his own woman, but blood is thick. Do not find this out the hard way with a cavalier outlook about a relationship with his woman.