I'm gonna give you the psychology answer:
insecurity...possibly rooted in childhood neglect (that he may not be aware of), but I'm not saying his parents are horrible.
For example: my parents are pretty good parents, but in the first few years of life they weren't around much because of the military and my mom was finishing college. So to this day I'm insecure about my relationships, thinking that they don't love me if they don't say it every 5 seconds. Or constantly worry that my boyfriend is going to leave even though everything is going great. I have to constantly resist the urge to ask him if/why he loves me...
My advice: Tell him you love him as often as possible without him asking you. and show him through your actions too!
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Most likely insecurity in himself.
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