Richard Burton, who left the website in August 2006, said the way in which the site now presents its personals section was "sadly typical of some of the more madcap ideas I would have strangled at birth".
At issue is the way in which photos from the personals ads service, which is powered by software from DatingBuzz, are juxtaposed with stories as a sidebar puff box.
"It shows a worrying lack of insight," said Mr Burton, who joined the site in 2001 but who left ahead of staff restructuring.
"This type of service is all about discretion. This is a world of cosy nicknames, box numbers and discreet introductions.
"I can't imagine anyone being too chuffed at posting a photo to an area I'd envisaged to be members-only and found it appearing next to the headline 'Scary Monster'. I'll give it 48 hours before the penny drops and someone chaperones them away from the public gaze."
Mr Burton, who was the third editor of Telegraph.co.uk, has previously said he left because changes at The Telegraph would have seen him go from 'manager of the first team to first team coach'.
He has since been a visiting journalism lecturer at Westminster and Cardiff.
Telegraph.co.uk has, in the meantime, seen wide-ranging new developments designed to increase participation, including the appointment of Mr Burton's news editor, Shane Richmond, as communities editor.
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