5. Anthony Wiener and Angela Merkel
This wasn’t exactly dating. Anthony Wiener wanted to improve his foreign policy credentials, and in typical Wiener fashion, he decided that the best way to do so would be to send foreign dignitaries d*ck pics. The only positive response he received from his endeavors was from German Chancellor, Angela Merkel, who reacted enthusiastically to the embattled former congressman’s penis.
The sordid ordeal was discovered by the NSA during their now infamous spying efforts on the German government.