The ninth episode of Season 2 of "My Life With The Walter Boys" kicks off with Alex confiding in Jackie his desire for a proper date. They agree to venture to Lockwood, a quaint town nearby, to catch a movie. Meanwhile, George and Katherine escort Will to a secluded section of the ranch where George had earlier discovered flourishing vines. George unveils his plan to cultivate grapes on the ranch and lease the land to Victoria's winery, hoping to expedite the repayment of their investors. Understandably, Will is deeply disheartened by this revelation.
To add insult to injury, Katherine drops another bombshell on George, informing him that Richard had used his own funds for this very project. Elsewhere, Richard extends an invitation to Jackie to celebrate Día de los Muertos with him the following day, but she appears hesitant. At school, Jackie seeks Grace's assistance in covering for her while she embarks on her date with Alex.
However, Skylar springs a surprise Halloween party, compelling Jackie and Alex to hastily affirm their attendance. In the football locker room, Coach Allen宣布 that three players, including Dylan, have tested positive in the drug screening. Dylan becomes enraged at Cole for failing to assist him in rigging the test, leading to a heated altercation between the two.
As Jackie and Alex brainstorm ways to sneak away for their movie date, Alex subtly expresses his wish to go public with their relationship soon. Jackie, however, isn't quite ready for that step. Additionally, she notices that her mother's perfume is nearly depleted, which disturbs her. Her mood takes a further dive when she fails her driving test.
As Skylar's party gets underway, Jackie finds herself increasingly irritated by the sight of a girl donning a skull-adorned face with floral accents—an apparent misappropriation of Mexican culture. Meanwhile, Skylar receives a call from Zach but chooses to ignore it amidst the festivities. Dylan, also in attendance, sports a sour demeanor, refuse Cole's offer of a beer. Kiley, privy to their earlier altercation, learns of the dispute. Dylan boasts about his father's donation to the school and his imminent return to the team on Monday, but Kiley disapproves of his conduct and storms off in a huff.
Elsewhere, George visits Richard's abode with a solemn resolve, announcing his intention to abandon their current venture. He then presents his idea for a vineyard with renewed enthusiasm.
As Alex and Jackie prepare to depart the party for the movies, Kiley sends Alex a desperate plea for assistance. Jackie encourages him to lend a hand, and Alex leaves promptly. Erin, witnessing this exchange, inquisitively asks Jackie why she's keeping her relationship under wraps, hinting at her earlier perception of a potential romance between Jackie and Cole.
Jackie unleashes her frustrations to Grace about Alex and her failed driving test, her eyes once again falling upon the girl in the skull attire. On the brink of confronting her, Jackie is intercepted by Cole, who gently inquiries into her distress. She confesses her upset over Día de los Muertos, feeling increasingly disconnected from her family and her true self in Silver Falls. Cole reassures her, affirming that she remains an integral Howard.
Arriving at Kiley's place, Alex finds her grandmother slumbering on the lawn, the victim of overindulgence. With gentle care, Alex assists Kiley in bringing her grandmother indoors. He suggests informing a teacher or an adult about the situation, but Kiley fears the prospect of ending up in foster care and hesitates.
They subsequently engage in a heartfelt conversation about the transformations that have taken place in their relationship. During this introspection, Kiley confesses to Alex an ill-chosen remark he made at Will and Hayley's wedding, stating that she was practically one of the guys. He hastily clarifies, emphasizing that he merely meant to commend her laid-back and cool demeanor. Despite Kiley's forced smile, they manage to reconcile.
Later, Cole escorts Jackie back to her place, where the evening evolves into a lively session of candy poker, joined by Danny, Isaac, and Nathan. The following day, Jackie commemorates Día de Muertos alongside Richard, savoring moments of camaraderie. Meanwhile, George broaches the topic of the ranch's new management plan with Will, who remains unconvinced and disheartened by the changes.
As Richard prepares to depart for New York, he entrusts Jackie with the key to his Colorado abode, symbolizing a bridge between their worlds. Embracing the opportunity, Jackie invites Alex over for an intimate date at the house. Concurrently, Cole receives his updated SAT results, a marked improvement from his previous attempts, offering him a tangible shot at college admission. Eager to share his triumph, he dashes to Jackie's place, only to stumble upon an intimate scene of her locking lips with Alex.
