Most Helpful Guy
Well you don't have to try. If the guy actually likes you in every way, he'll tell you truth no matter what the situation is. He won't hide anything from you (like his phone etc).
How to find out if he's telling truth is the right question. But as i said the more you talk and spend time together the more you'll get to know.
Most Helpful Girl
Are you seriously almost 40 and still this insecure? I mean it's one thing to want your partner to compliment you, but to ask them to compare you to other women and rate you is ridiculous and just going to end badly for everyone involved. It should be enough that they find you attractive and want to be with you.