My father never had any of what would be considered "THE" talks with me. He pretty much stayed out of my life even though we lived in the same house. I'm a little mixed on the don't embarrass by asking or talking about it views. In some ways I wish my father had talked to me about these things when I was younger, but then on the other hand I had a bit of a chip on my shoulder growing up and probably would have felt insulted by it. Of course that chip was probably due to his lack of interest in me or anything I did. One thing I know for sure is, I know I would have been much more comfortable talking to him on a man to man level about women. More along the lines of hey what do I think of this or that or maybe some guidance on how to act with girlfriends. To be completely honest, I've never been good with women. I'm very shy at first and I really have no idea what to say to someone I don't know. I didn't even have a girlfriend until I was 16 and she came at me (guess that supports the whole women are so aggressive men don't have a chance quote). It's obvious he's in the stage that you need to talk to him, but the way you approach it will make all the difference as to whether he comes to you when he needs advice or pulls completely away. Treat him like your equal, as though he's a friend you've known all your life, lost contact with and are just getting back together and finding out what each other has been up to. Dad's can be very threatening to young men that are trying to do their own thing. Especially if there's a control issue there or maybe an embarrassing moment that sticks in his head. In any event this is the time to get involved in his life more than ever. Not invasive, just a friend on the outside looking in. I think back on my life and I really wish my father was around more when I was growing up. To this day I still can't talk to him about anything of a personal nature. most of our conversations consist of "how's work, anything new? Ok have a good day." Just some food for thought.