As members of Bravo team travel to New York City, they reflect on a day that shaped each of their lives forever.
Mickey and the kids are forced to downgrade after their financial adviser cuts them off due to excessive spending; Chip learns tricks from Jimmy on how to live in a luxurious hotel.
As Riley (Jennifer Love Hewitt) invites unwanted scrutiny when she volunteers her staff for a fundraiser, Evan (Colin Egglesfield) joins a prostitution task force that threatens to target the Rub.
Faced with mounting bills at work and at home, Riley (Jennifer Love Hewitt) considers seeing a client who offers $50,000 to spend the night with him.
As she works to keep the Rub open and out of trouble with the police, Riley (Jennifer Love Hewitt) must avoid being implicated in her husband Kyle’s (Brian Hallisay) crimes and winding up in prison, too.