James Nightingale, played by Gregory Finnegan, is a villain on Hollyoaks. James works as a solicitor and in his first scenes he offers legal advice to Cindy about divorcing Mac. Waring described James as a suave and very mysterious man. She told Laura Morgan of All About Soap that James overhears Cindy talking to Tony Hutchinson (Nick Pickard) about committing bigamy and he offers her legal assistance. She views him as a handsome man and uses her sexuality to get what she wants, James' help to escape bigamy charges. Waring added "he's very alluring and dashing, so of course Cindy is immediately taken in by his knight-in-shining-armour routine."
It was revealed that James is the eldest son of already established character Mac Nightingale, the older brother of Nathan Nightingale and Ellie Nightingale and the half-brother of Alfie Nightingale. It was also revealed that James teamed up with his mum Marnie Nightingale with the help of Cindy so they could drain Mac of every penny.
Marnie, with the help of James, attempts to persuade Diane O'Connor and Tony Hutchinson to sell The Hutch to her in an attempt to get closer to her children. However, their several attempts fail. The pair then steal Diane's laptop to see whether if the restaurant is close to bankruptcy. It is then revealed that the restaurant could be bankrupt by Easter, so she and James then return to the restaurant in a bid to persuade Diane and Tony into selling the restaurant. However, Diane's nephew Scott Drinkwell catches them with the laptop as they return it. Marnie later learns that Tony earned money from betting with Darren Osborne (Ashley Taylor Dawson). She later informs Diane of this, leaving her upset.
After Ste Hay and Harry Thompson, he offers them a place to stay, which is the shack where Cameron Campbell (Cameron Moore) held his brother Lockie Campbell, hostage last year. When Ste is given a two week trial at The Dog in the Pond, James tampers with the drink dispenser so he can sabotage his chance of getting a job. When Ste pulls the dispenser, the alcohol goes everywhere. Ste and James then change their shirts, but when Harry sees them, he believes Ste is cheating on him, making him storm out in anger. James later reveals to Harry that it's not Ste he's after, but he is in fact after him. Ste and Harry later have an argument over Ste's job, which causes Harry to furiously storm out of The Dog. Harry later hitches a ride from James after the heated argument. James later offers Harry £10,000 so he can sleep with him for one night. Harry refuses the offer because he loves Ste too much to do it. However, James will not leave him alone until he says yes.
While Ste is looking after his son and daughter, Leah and Lucas, they go to the Tug Boat so they can eat. After they've eaten the food, they run off as Ste doesn't have any money to pay. Cameron later calls the police and him and Ste have a fight, in which Ste accidentally hits a police officer. Ste is later arrested for assaulting a police officer and James says that he has been fined £300 as punishment. After his arrest, Amy Barnes (Ashley Slanina-Davies) turns up after Harry phoned her about what happened. Amy and Ste argue over what happened. Amy is so angry with Ste that she bans him from seeing his children for good. Ste later blames Harry for him from being banned from seeing his children and for everything that has happened since his arrest. Ste and Harry continue to fight over what happened, and Ste almost breaks up with Harry because of it. After their argument, Harry phones James and later accepts his offer and they later have sex. Unbeknownst to him, Leela has allowed him and Ste to move back in with them.