Detective Annie Ryder and her small town are rocked by the disappearance of local teenager.

The search for Jesse Sweetland continues as Annie and the detectives dig into Annie’s compelling theory, and end up with their first real lead. Annie confides in Peter about the return of her mystery Riddler, and he demands that she stay away from the guy while Peter works to find him. Annie works to repair her relationship with her 12-year-old daughter Daisy after an incident puts them at odds, but she finds it hard to focus on family when there are so many high stakes unanswered questions all around her. Virginia tracks down Jesse’s boyfriend Danny Debessage, who provides her with a piece of vital information about the night Jesse went missing. And despite Peter’s warnings, Annie finds herself following the new riddle left for her by the Riddler, with shocking results.

As Annie and the cops reel from a shocking discovery, Annie comes clean to Peter about things the Riddler gave her, and shares her theory that the case of missing Jesse has a connection to the case of murdered Sandy from twenty years ago. Peter reluctantly agrees to let Annie continue her relationship with the Riddler in the hopes of it bearing fruit. When a riddle is found at the new church, Annie is led down an uncomfortable path that has her digging into a loved and respected member of the community. Virginia and Brady make a discovery that takes the Jesse case in a very different direction - a direction that Annie doesn’t buy. In home life Annie finds herself at odds with Eddie, Daisy’s father, and Annie’s on again, off again love, over how to deal with Daisy’s newfound risky behaviour. In the end Annie gets a glimpse of the very real and dangerous angry side of the Riddler.

The cops search a drug house and find evidence to bring the house’s owner to the station. Annie feels the dealer is all wrong for Jesse’s disappearance, but the evidence is hard to argue with. Annie goes it alone, digging into a side investigation on who her Riddler might actually be. Tensions rise between Annie and Peter, as does mistrust and the knowledge that there are secrets between them. Eddie begins to pull away from Annie, finding a connection with Brady’s sister Briana. Despite a major break in the case Annie feels at odds with her fellow cops, and continues her investigation into the Riddler and finds herself face to face, in a very unusual way, with the man who it could be.

Annie digs into a new theory that drugs found in Jesse’s room were planted. An oddity about these particular drugs sends her down a path of investigation to find out whose drugs they truly are. Her relationship with the Riddler enters a new phase as he begins to share information with her in a new way. He makes shocking revelations to her, further solidifying her theory that the case of missing Jesse is somehow connected to the case her father couldn’t solve years ago – and the one that her father killed himself because of – the case of murdered Sandy Driver. An emotional funeral is held for Jesse, but cut short by chaos stirred up by Annie. As Annie digs into the drugs angle, it takes her down a shocking path that yields results. Eddie’s relationship with Briana progresses. Peter and Annie drift further apart, only to have him tell her something that makes her regain some trust in him. In the end it is Annie’s trust in the Riddler that is truly tested.

With the arrest made in Jesse’s disappearance, one that Annie doesn’t buy, she is at a dead end. Fully believing now that the cases are connected – she decides to dig into her dad’s old notes on the Sandy case with the idea that using what she knows now, combined with what he knew then, maybe she can find answers in the Sandy case. If she can, it’s possible she can find the connection and then the truth in the missing Jesse case. This path leads her to a new member of the community, and unearths a shocking revelation from twenty years ago, that has emotional ramifications for Annie. Peter gets a call from a source giving him a lead on Annie’s Riddler, while Virginia makes a discovery that causes her to rethink everything she thought about the Jesse case. With Annie’s emotions raw, she makes an attempt to pull Eddie away from Briana which ends in chaos. Suddenly she finds herself emotional and alone, wondering where the Riddler is.