Diana Payne is a wealthy businesswoman from Los Angeles who masked as Chuck Bass's mother throughout the fifth season. She kept the secret that Bart Bass was alive and was being paid to do so by Jack Bass.
Nate meets her in the season five premiere at a party hosted at her house. The two then meet again in new York, and she is revealed to have moved to New York as she's the new owner of The New York Spectator. She hires Nate to work at the Spectator. After persuading Nate to take party guests cell phones from the Jenny Packham fashion show, she and Nate come across Ivy Dickens' phone. The phone has Serena's number in it, yet no one knows anyone named Ivy. Charlie (Ivy) is worried about losing the phone as it has incriminating evidence of her secret on it. Diana meets Charlie Rhodes (who is actually Ivy Dickens), and suspects that she is Ivy.
Diana calls Charlie and purposely asks for Ivy Dickens in order to extract a confession that she is in fact, Ivy Dickens. Diana uses this information to blackmail 'Charlie' into working for her. Eventually, Diana fires 'Charlie'.
Nate's Grandfather William is revealed to be the financial backer for the spectator. It is made clear that he hired her to groom Nate to take over the spectator. William demands she resign in order for Nate to take over.
After Chuck and Blair's car accident, she is called by Jack Bass. Jack informs her of the accident. When she asks how bad it is, Jack says he wouldn't have taken a big risk like calling if it wasn't serious. She says she'll meet him there.
Chuck had been led to believe it was Jack who donated blood to him that saved his life. When Chuck finds that wasn't the case, he had his investigator look for whoever gave him the blood.
Serena overhears a phone conversation between Diana and Jack. It is then revealed that it was Diana who donated the blood. Serena goes to the hospital and asks a nurse if she recognizes Diana. The nurse tells Serena that Diana arrived at the hospital on the night of the accident, donated blood, and left quickly.
Later, Serena confronts Diana, asking where she was the night of the accident, chuck's blood type, his birth date and where she was on that date. Diana tells Serena she is Chuck's mother. Their conversation was streamed live to Gossip Girl, which resulted in everyone finding out the truth, including Chuck.
Diana goes to the Empire to talk to Chuck. She tells him she met his father when he was still with his wife. They had an affair and it ended when she got pregnant. Chuck asks why she gave him up. Diana tells him that she was a mess, mixed up in the wrong things with the wrong people; unfit to raise a child. She tells how Bart's wife Elizabeth couldn't get pregnant, and it seemed like a way to solve all their problems, so she left town alone and ashamed. She tells Chuck that a few years later, when she'd heard Elizabeth had died, she returned and wanted desperately to see him, but Bart thought it would be too confusing for him. This is revealed in the next episode to be a lie she used to cover up the fact that Bart was still alive and in her brothel; another thing she tried to keep secret. She is not Chuck's biological mother. In The Fugitives, Nate lets her leave, without her name being put in print.
-xoxo Gossip Girl.
- Season 5