Maybe try mixing it up. Don't ask how he is for awhile. If he asks you, be mysterious... don't give him much detail and leave him wondering what you're up to. If you've been out with friends, you were just out; period. Keep it short and you'll avoid the feeling that he's not interested, and if you usually ask how he is, and then stop, he may be curious why you don't seem to make the small talk anymore.
