VIDEO: Kelly Cutrone On Why Dads Don't Make Good Wingmen

Whaddya get when you unleash one beautiful, sophisticated young woman -- who's newly single and ready to mingle -- on a city known for its strong percentage of egotistical man-children? A whole lotta crap dates, including one candlelit dinner for two three with a father-son tag team.

Yes, we're talkin' 'bout Freddie Fackelmayer ... and the time he surprised Whitney Port by reserving an extra seat at the table for dear ole dad. It was actually this incredibly lame move that made it more of a relief than a disappointment when he surprised Whit a second time in the Hamptons by copping to having a girlfriend. And while we'd hoped Fred would be the last d-bag she'd encounter during Season One of The City, inevitably there were plenty more of these suckers just waiting around the corner (from LV, that is).

Last week, we invited Kelly Cutrone into the office to review some of Whitney and Roxy's most dubious relationship moments and offer her take on what could've been done differently. Check out what she had to say about Fred Fack's daddy issues, plus click here for more of her commentary on other show shockers.