Uma noite de paixão leva Charlie, um vigarista, e Emma, uma agente disfarçada da CIA, a se apaixonarem. Entretanto, eles não sabem que estão em rota de colisão profissional. Enquanto Charlie foca nos “negócios da família” para poder largar o ramo para sempre, Emma se aproxima do criminoso que detém as dívidas da família de Charlie e que os força a reconhecer as mentiras que contaram para salvar a si mesmos e suas famílias de consequências desastrosas.

Após Daphne definir rapidamente uma solução para o pagamento, os Nicolettis elaboram um plano para roubar um colar valioso em um leilão. Enquanto Emma e Charlie perseguem Daphne, seus mundos quase colidem.

The Nicolettis persuade a wealthy woman to seek revenge on her con-man fiancé at a horse race. Meanwhile, Emma meets Charlie’s family, and the CIA and Nicolettis catch wind of Daphne expanding her business beyond the Maguire drug enterprise.

Daphne enlists the Nicolettis to steal a book of blackmail from a DC fixer. Later, Charlie puts his relationship with Emma on the line to ensure her safety.

Birdie reaches out to an old flame to help the family steal a painting. Meanwhile, Emma grapples with Charlie’s admission and must deal with conflicts of interest at work at the CIA.

Charlie becomes Emma’s new CIA asset and is tasked with spying on Daphne while they attend the event together, causing Emma to feel jealous. Later, Leo reveals to Birdie the real reason Simon abandoned her and Ollie.

Daphne tries to use Charlie to help Patrick get out of jail. Elsewhere, Emma partners with Birdie when Leo gathers his old friends around to con a man who lost their pensions years ago.

Realizing they want the same thing, Emma and Daphne agree to work together to take down the Maguires. Later, the Nicolettis consider selling the bar when a great offer comes their way, and David announces he is done with politics.

Emma and Charlie partner with Daphne to produce a plan to take down the Maguires once and for all, but will the final showdown cause Charlie and Emma to stay on opposite sides or end up closer than ever?