You need to tell the guy straight out if you are interested in him (more than a friend). He obviously likes you more than a friend but doesn't want to ruin your friendship if you were to reject him. On the male perspective, this is a disastrous situation. No wonder he doesn't want to hear about your dates. He likes you! He is being forced into the role of the "Intellectual Whore." You use him for comfort, intelligent converstations, advice, but he doesn't "get any" in the end.
Check this site out for the best explanation:
http://www.intellectualwhores.com/masterladder.html
Intellectual Whore defined: "Basically this is just a guy who has a very high position on the friends ladder. So far up the friends ladder that he gets the dubious honor of getting to provide all the intimacy that a girl is missing when she's off fucking guys who basically don't care about her like outlaw bikers and band members. So he gets to be the proxy father/confessor/friend/teddy bear for her, depending on what she is missing at the time."
Just straight up tell him if you like him or not. Depending on the type of guy he is, he may either 1) never talk to you again, or 2) be at ease around you, knowing nothing will ever happen. (1 and 2 are providing that you DON'T want him more than a friend)
Sounds like if you were to like him, you guys would be good together. Sounds like a nice guy. Sounds like I used to be around girls. You just end up getting your heart broken.