The ninth episode of Season 2 of "Cruel Summer," set against the backdrop of autumn 1999, kicks off with a nostalgic glimpse into Luke's childhood, a time when his mother's presence still warmed their home. In the present, Luke finds himself poring over vintage family footage, reminiscing about the joy they once shared and pondering over the fate of his father subsequent to her passing.
As the trio—Luke, Brent, and Steve—gathers around the pool to commemorate their late mother's 44th birthday, Steve busies himself preparing a feast. Brent, in a playful yet harmful manner, attempts to submerge Luke in the water, only to be halted by Steve, who urges Brent to let it go and tells Luke to not overreact to his brother's antics.
During the cake-cutting ceremony, the brothers fondly recall memories of their mother. Steve remarks that Luke's demeanor reminds him of his deceased wife, a statement that stirs jealousy in Brent, who mocks Luke for being overly effeminate, leaving Luke heartsick.
With the school year's inception looming, Luke opts to spend quality time with Megan and Isabella rather than joining his male friends. Isabella teases Luke by asserting her closer bond with Megan and challenges them to a compatibility test, which Luke fails miserably while Isabella shines.
The boys mock Luke for prioritizing girls over their brotherhood. Days pass, and Luke and Megan return home from high school, where Luke confides in her about his estrangement from his father, whose interests diverge widely from his. He reveals that Megan has become the pillar of his life since his mother's demise.
After school, Luke confronts his father, who reveals ambitious plans to transform their town into an eco-city, brimming with luxurious leisure activities. Luke, visibly distracted, confesses his contemplation of forsaking college. Steve, incensed, insists that he couldn't support a family as a coastguard.
Luke tries to reason with his father about his true passion, but Steve remains unconvinced, asserting that a beach outing couldn't sustain a livelihood. He argues that a coastguard's salary couldn't replicate the affluence he grew up with.
Luke seeks solace at the Sheriff's station, where Meyer discusses his Coast Guard application. Luke reveals his hesitation in disclosing his decision to his father sooner. In the privacy of his bedroom with Megan, Luke expresses his desire for their lives to remain unchanged and maps out their shared future together.
October 1999
The narrative shifts to October 1999, where Luke, Megan, and Isabella are busy dressing up for Halloween. As Luke and Isabella engage in conversation, Isabella encourages Luke to pursue his own aspirations rather than chasing after Megan. She insists that hovering around Megan will only hinder him, as she is already Megan's confidant in mischief, a role Luke cannot usurp.
A couple of days later, Luke finds himself with Brent and their friends at the Chambers House. Brent, with a sinister smile, reveals that girls secretly enjoy being filmed during intimacy and boasts about often capturing their moments without their consent, aiming to unveil their true, wild selves. He dares Luke to elevate his game if he wishes to keep Megan by his side.
On a subsequent night, while Megan and Isabella are out celebrating, Luke anxiously awaits Megan at the Landry House. Megan apologizes to Luke for forgetting their planned hangout. Isabella, sensing an opportunity to stir drama, hints that Megan was the center of attention at the club, igniting Luke's jealousy.
Later, at school, Luke and Jeff clash. Jeff accuses Luke of mirroring Brent's bad behavior and scolds him for pursuing Megan without discussing it with him, despite knowing Jeff's feelings for her.
December 1999
As December rolls in, Isabella, Luke, and Megan spend time together, with the girls excitedly discussing their plans to travel and explore the world. Luke feels excluded and overwhelmed by the secretive plans the two girls have made without him.
The following day, Luke shares with his father that he has been accepted into Branson and reveals he also gained admission to the Coast Guard Academy. Steve, thrilled about Luke's acceptance into Branson, urges him to abandon the idea of joining the coastguard. However, Luke stands firm in his determination to follow his dreams. Steve, frustrated, lashes out, expressing his weariness from constantly trying to guide Luke.
The duo engaged in a heated argument, with Luke conceding that it would've been more beneficial for the family if Steve had perished instead of his mother, the sole soul who truly understood him. Luke subsequently arrived at the Landry House, seeking solace in conversation with Megan about his altercation with his father. He confessed to her his desire to flee and embark on a fresh chapter in life.
The narrative shifts to the evening of the Christmas gala, where Luke, driven to desperation by his father's yelling and coercion to join Branson, inadvertently leaked his intimate tape with Megan. Days following the incident, the boys debated Luke's impossibility of creating such a tape with Megan, yet somehow, he had done so—but with Isabella. Luke reveled in the attention he garnered.
A few days later, Luke and Megan found themselves in the cabin, with Megan's paranoia about being filmed reaching a crescendo. Luke endeavored to reassure her, vowing to shield her from such worries. Left alone at home, Luke was startled by his father's unexpected arrival, inquiring about his absence from Megan's side.
Luke sensed a shift in Megan's demeanor towards him since the tape's leakage, prompting Steve to advise him to move on. He likened girls to the abundant fish in the sea, suggesting that Luke had numerous options to choose from.
January 2000 saw Isabella discharging a firearm, the bullet grazing Luke's ear. Megan, worried sick, rushed to stem the bleeding. Isabella, fearing that the gunshot might have been heard, urged Megan to abandon Luke and flee. She insisted on being left alone with Luke to ponder over his actions, but Megan hesitated.
Isabella seized the videotape, intending to use it as leverage against Luke, demanding that he keep the cabin incident a secret. As she stepped outside, Megan stayed back, attempting to assist Luke. Luke, desperate for forgiveness, pleaded with Megan, while Isabella awaited her outside.
To Luke's astonishment, Megan revealed that she was pregnant. Panicked and fearing his father's wrath, Luke suggested that Steve might help terminate the pregnancy. Megan, disgusted and upset by his reaction, called him a jerk and left him tied to the bed in the cabin.
Luke awoke some time later, struggling to free his hand from the ropes. With perseverance, he managed to break free, dressed, and headed out of the cabin, fury burning within him. He reached the dock, where he waited anxiously for someone to arrive.
As he waited, Luke's thoughts drifted to the numerous instances where his family, friends, and townsfolk had mistreated and provoked him. The episode concludes with Luke engaging in a heartfelt conversation with the person he had been eagerly awaiting at the dock.