I don't think either you nor he should be quite so focused on the other person. What do you want for you? I would be wary of his asking too much whether you love him or not (he needs more self esteem and confidence about himself) and trying to compare who loves whom the most/best? Love isn't just feelings, it's actions. How you treat each other "says" a lot about how you care for each other.

Feelings are like weather and ebb and flow; we don't feel happy all the time or anxious or bored, angry, or any of our other feelings and we won't necessarily feel "loving" all the time even though we are with someone we love. Learn how your own feelings "work" so you can be comfortable with yourself and how you relate to others; that's what feelings are for, to help us with our relationships to ourselves and others.