Spending weekend with me

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A friend of mine, whom I go to college with will soon spend a few days at my house. I have noticed that recently he has become more distant (not intentionally, that's just the way it has worked itself out). An observation that I have made is hat while we enjoy each other's company, he like's my sense of humor and I can keep him entertained, sometimes if we are together for an extended period (like for a long trip), after a while I can't think of anything to say. Sometimes silence is good. But, too much is bad. I think that he is the type of person who wants me to make sure that I can keep him entertained if he can't think of anything to say (but not to the point where I am talking so much that I am annoying).

Part of my problem is that since our school is so small, and since we started at the same time, we are together for a lot of things anyway so it really doesn't make much sense to ask about things that are going on in his life (except at home, and he keeps alot of that to himself).

So my question is, does anyone have suggestions about things to talk about to kill a dead silence with someone that you are already close too, and can talk about a number of things with already but seems bored (and in turn becomes more attracted to people that can better entertain him) sometimes. NB: I think he might have ADD.

i suggest you boil a cup of black tea and sugar
or a cup of instant coffee with brown sugar or light cream
something to pass the time. maybe go outside and sit on the bench? i find i do not have to talk to some of the male friends of mine we can just walk around outside talking little or playing basketball silently. in fact a lot of the communication is kind of non verbal and if you know the dude for a long time than you do not really have to talk in order to be friends, if that makes any sense to you.

or

just turn on the TV

Ask him something random. "Is she hot?" "What's the best song ever?" "Would you have a threesome with Megan Fox and John McCain?"