The reason Caroline has never done anything she regrets with a man because in her head, it's Ashlee doing those things.
At first it seems odd that someone with a graduate degree in business can't find better work than a waitress at a diner, until you realize that the kind of companies that typically hire people with business degrees are also the kind of companies who wouldn't want to be associated with the family of a convincted embezzler.
Then again his sister seems to have no trouble with her business. To be fair cosmetics don't exactly scream white collar crime then agin neither do cupcakes.
Also the possibility that they might believe that Caroline's father simply bought her business degree.
Oleg once joked about having sex with Sophie only for her to wake up 'mid-coitus'. Meaning he was having sex with her while she was asleep. Oleg is more than a creep, he's a full blown rapist.
In the "cold open" to "And the Past And the Furious" Han brings in a CPR dummy named Judy for the staff to practice. Oleg greets Judy by name, and when questioned he says "With a torso like that, she really gets around." What makes the comment this is that the face of the standard CPR dummy is based on the death mask of a drowning victim. It says all kinds of things about Oleg who is already creepy.
