Thinking about it some more, the scripted interactions didn't work because they seemed too much like begging, especially after the 2nd message, when a normal person would have simply stopped communication with a non-responder.
There was no mystery or enigmatic friction created in his scripted messages. Nothing to raise the "buying temperature" or whatever you want to call it.
Also a head and shoulders shot with no context is as bland as can be. At least 1 shot should have been with an outside interest, like, with your dog (if you have one) or with friends showing you enjoying yourself. By adding such photos, I am willing to guess his responses would have been better.