Troubling enough is a 51-year-old man pursuing a 14-year-old girl* but the sheer, brazen stupidity of the method is astonishing.
This JSOnline.com report contains a link to the criminal complaint against Racine, WI mayor Gary Becker, to which is attached a copy of the Yahoo! instant message transcript (Be warned: it's vomitous).
I'm no psychologist, but it seems to me that the degree of raw pathology required to engage in this sort of alleged behavior has to be close to equivalent in severity to the borderline pedophilia.
Similarly, the subject needs equal parts punishment and help.
* Or even a police officer masquerading as one.