How Do You Know (2010) Timeline Explained – Every Event in Order

George calls Lisa because a mutual friend encouraged him to reach out. However, he's not trying to pursue her romantically, he simply calls to update her about his serious relationship with his girlfriend. The call is more about fulfilling a social obligation than expressing genuine interest in Lisa at that point.

• george madison
• lisa jorgenson
• phone call
• relationship

George's girlfriend ends their relationship during his time of greatest vulnerability, when he's facing a federal investigation and has just been dismissed from his job. She abandons him precisely when he needs support most, which deepens his emotional distress and makes him more receptive to reconnecting with Lisa.

• george madison
• breakup
• job loss
• investigation

Lisa moves in with Matty seeking comfort during a difficult period. She's just learned she didn't make the Team USA roster, adding to her emotional struggle. Matty offers material security through his lavish penthouse, and she chooses that stability over the uncertain connection with George after their dismal lunch date.

• lisa jorgenson
• matty reynolds
• moving in
• penthouse

George proposes an ultimatum to his father Charles: if Lisa chooses to be with George, Charles will face criminal consequences for the corporate wrongdoing. If Lisa refuses George and chooses Matty instead, George will accept full blame for his father's crimes and go to prison while his father avoids serious charges. This forces Lisa to make a choice that determines both their fates.

• george madison
• charles madison
• deal
• ultimatum
• prison

Charles agrees because he's facing life imprisonment due to prior convictions, while George would likely receive a lighter sentence. Charles is willing to sacrifice his son's future to protect himself from severe consequences. The deal allows him to escape accountability if Lisa rejects George, making it a self-serving proposition.

• charles madison
• george madison
• father
• prison
• corporate fraud

Lisa chooses George because she realizes authentic connection matters more than superficial security. Matty offers wealth and a luxurious lifestyle but remains emotionally unavailable and unfaithful. George, despite his modest apartment and legal troubles, offers genuine emotion and vulnerability. Lisa's line about George being the only thing that doesn't feel silly reveals she values sincerity over material comfort.

• lisa jorgenson
• george madison
• matty reynolds
• choice
• love

The bus scene symbolizes Lisa and George embarking on a new journey together despite uncertainty. By choosing to take the bus rather than rely on Matty's car or Charles's wealth, they embrace a simpler, more authentic path forward together. It's a visual representation of choosing genuine connection over material security.

• bus
• ending
• journey
• new beginning
• choice

Matty's penthouse is in the elite building owned by Charles Madison, George’s father. This coincidence creates the setting for the pivotal encounter between George and Lisa in the building's lobby. When George helps Lisa with groceries, it reignites their connection and sets in motion the events leading to her final choice.

Foreshadowing: The building connection is established early as Matty's lavish residence and later becomes crucial for the chance reunion.

• matty reynolds
• penthouse
• charles madison
• building

Annie, George's pregnant secretary, remains loyal to George despite his legal troubles. She tries to provide him with insider information about the company to help his case. George, however, urges her to protect her own job since she has a baby on the way, showing his selflessness even in his darkest moment.

• annie
• secretary
• george madison
• loyalty
• pregnancy

George is caught in the crossfire of a federal investigation into corporate wrongdoing at his father's company. Even though Charles is actually responsible for the illegal activities, George was employed there and becomes implicated in the investigation. He faces the threat of prison time simply by association, while his father orchestrated the crimes.

• george madison
• charles madison
• indictment
• corporate fraud
• investigation

Matty organizes a birthday party for Lisa as an attempt to win her back and salvage their relationship. The party becomes the setting for George's public confession of love, where he asks Lisa to find him downstairs if she feels the same way. Matty's gesture, while thoughtful, can't overcome the fundamental incompatibility between them.

• matty reynolds
• birthday party
• lisa jorgenson
• reconciliation attempt