He's asking them due to insecurity. Indulging him isn't going to do either of you any good. Tell him from now on you refuse to answer such questions. Let him know that it is taking a toll on the relationship and it puts you in a really unfair position. He needs to get to the bottom of his feelings of inadequacy, and doing so with a therapist would probably be best.
Don't get married until this issue is resolved entirely.
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Rise up above it, high up above it and see.
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