In 2009, Michael is giving a lecture on Wuthering Heights when Helena visits him in class. Michael then has some of his students open their books, spelling out the message "WILL YOU MARRY ME" to Helena, which she happily accepts. That afternoon as Michael and Helena leave together, she mentions that she told her father the good news and he wanted to throw an engagement party for them. Suddenly, an ambulance arrives and a woman rushes outside, carrying an unconscious student. As the student is taken away, Michael finds out he overdosed on ecstasy pills.
That night over dinner at the Bertinelli Mansion, Helena informs her father of the incident and requests that he cease his work with the ecstasy pills' dealer, Tony D'urso. Frank expresses his condolences but justifies the work as "business". A furious Helena points out a kid nearly died due to his so-called "business" and they get into a heated argument. Frank states that everything he does is to provide for their family before storming off.
At Helena and Michael's engagement party, Frank gives a toast and congratulates the couple. He expresses his hope that Michael will join the "family business", claiming he will need a larger salary to support his daughter. However, Michael politely declines, wanting to continue teaching. As Michael and Helena dance, Frank orders his right-hand man, Nick Salvati, to check out Michael.
Later one night, Nick searches through Michael's apartment and finds a laptop. Upon seeing the information it contains, Nick calls Frank, revealing that Michael has (supposedly) gathered enough evidence to send them to jail and was just about to hand it over to the F.B.I.. Shortly after, Michael returns home, expecting Helena, and Nick shoots him. Helena later arrives at the apartment and finds Michael dead, much to her horror and devastation.
Sometime after Michael's death, Helena moves back into the Bertinelli Mansion. Whilst mourning her fiancé, Helena wakes up late one night and walks downstairs. She overhears her father speaking on the phone, confirming that Michael's murder can't be traced back to him and believes Helena will soon understand his reasons. Shocked, Helena realizes that Frank was behind Michael's murder.
At Michael's funeral, an unsuspecting Frank tries to provide emotional support for Helena. Tony appears and apologizes for her loss, offering Helena some of his product should she need it to cope with the pain. After everyone leaves, Helena tosses a rose into Michael's grave.
Over a year later, Helena has begun a crusade against her father and his associates. She tracks down Tony in the midst of a drug deal with another teenager and shoots him dead, stating that "it's a start" to avenging Michael.
Helena then flashes back to the present. Oliver wakes up and asks if she is all right, wondering if she had a bad dream. Helena responds, "Yeah, but I'm awake now".