Either he doesn't understand, or he doesn't know how to make the conversation work. For a guy, it's like being in the middle of a hockey game; you are playing hard and following the rules, but then suddenly the rules change and the puck is gone and the score is measured in smiley faces. And then miniature horses come out onto the ice and start galloping all miniature horse-like! And suddenly all the other players start singing songs in unison and yelling, "We're winning, we're winning!" (I have had nightmares like that.) This is how lost guys can feel when they are trying to follow along with a talkative girl. There isn't a right or wrong way; we're just very different.
The ponies should be robot dinosaurs and instead of smiley faces they're angry clowns with pancake cannons. It's not a nightmare until you realize the puck is a small fusion reactor and the net somehow transcends spacetime and you're looking into your own mouth, but you can't stop because... you have no idea, you just can't. Then the dinosaurs are screaming because you skated over them, but your skates are chainsaws and the clowns are really FBI agents knocking at your front door asking where are your children? and you think not again, I don't know sir, why? We believe they're responsible for breaking the moon this time.