Remember back in 2006 when Ashley Davenport was working for a Russian whore house? Those were good times. Turns out girlfriend just wanted to put her Art History degree to good use, which naturally led to a life of prostitution and spandex dresses.

Luckily, Ashley was able to put her nefarious past behind her and climb up the social ladder, but now that we know she was a hooker, certain moments have been rendered all kinds of awkward. To wit:

1. That One Time Ashley Planned Conrad and Victoria's Wedding
Ashley was put in charge of planning one of the most important weddings the Hamptons has ever seen. However, we have a feeling Victoria would have been less than thrilled about Ashley's involvement in the nuptials had she known Ash was a former Russian escort. Then again, Victoria murdered a dude when she was a teenager, so who is she to judge?

2. That One Time Ashley Hooked Up With Daniel
Daniel and Ashley's drunken hookup was already 50 Shades of Sketchy (Team Demily for life), but little did we know she was Julia Roberts to his Richard Gere. Yep, Ashley totally pulled a Pretty Woman and wooed one of the wealthiest men in the Hamptons. The only differences are that Ash would never wear pleather, and Daniel had no idea she was a former hooker. Do you think Danny Boy would have gotten frisky with Ashley had he known about her sordid past, though? Probably, guys. Poets don't judge.

3. That One Time Ashley Had a Job at Grayson Global
Look, it's not like Grayson Global has particularly high standards for their employees — most of them are semi-drunken former murderers with ties to various terrorist groups. But even Conrad might have wagged his finger in horror had he known that Ashley used to be a prostitute. After all, this British bombshell got pretty high up at Grayson Global, especially considering that her former business experience consisted of "How to Fail at Art History."

Do any scenes pop out at you as totally awkward now that we know about Ashley's past? Hit the comments!  


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