Most Helpful Guy
Insecure, I guess. I'm still in awe that I have this gorgeous lady sending me affection online and stuff (from America, so nothing can happen), she thinks she's worthless and keeps telling me I deserve better. I tell her she's beautiful and sweet and I'm a mess xD (ah, abuse survivors "dating," it's a barrel of laughs lol) If I was to play armchair psychologist I'd say he was feeling insecure after you talking about being pursued by other guys and questioning his value to you when you have so many other options, and he likely doesn't, so clearly you're more ind emand than him, and more of a catch.
Most Helpful Girl
He is insecure and he wanted to hear some reassuring words