The fourth episode of "My Life with the Walter Boys Season 1" starts with a small but emotionally charged incident: Parker accidentally breaks Jackie's teapot, which seems to hold much more sentimental value than it initially appears, leaving Jackie visibly upset. This scene subtly hints at a deeper connection Jackie has with the teapot.

At school, Alex notices Jackie's low spirits and inquires about it, but Jackie keeps her troubles to herself. Later, Jackie's triumph in a race, followed by her appointment as the squad leader by the coach (who is also Erin's mother), adds to Erin's frustrations. This decision causes a rift, especially when Erin's questioning of her mother's decision backfires, leading to her own public embarrassment.

Meanwhile, Cole picks up on Jackie's downhearted mood and persuades her to skip class and join him at a lakeside party. Initially hesitant, Jackie eventually gives in to Cole's encouragement to relax and have fun. The party, however, takes an unexpected turn during a game of truth or dare, leading to an almost-kiss between Cole and Jackie. Unfortunately, Jackie's drunken state results in her vomiting on Cole, adding a comedic yet awkward twist to the moment. This event also underscores Cole's internal struggles with his friend taking over his football jersey number following his accident.

Upon returning home drunk, Jackie and Cole face consequences from Katherine and George, who ground them. However, Jackie receives a softer reprimand due to her usually good behavior and studious nature.

That night, Alex brings Jackie a hangover remedy, leading to a heartfelt moment where Jackie expresses her gratitude for his support since her arrival. The moment nearly escalates into a kiss, but Alex, considering Jackie's state, steps back to avoid any potential regrets.

The next day, while the Walters attend the Lark after Dark inauguration, Jackie and Cole, still grounded, stay behind to complete their chores. Their time together leads to a revealing game of Truth or Dare, where Jackie confides in Cole about her sister and the teapot's significance. Cole, in turn, shares his feelings about the aftermath of his accident and the impact on his football career.

The episode reaches a climactic moment when a blackout occurs, creating an intimate atmosphere between Jackie and Cole. However, this is interrupted when Alex walks in, witnessing a moment that appears to deepen the love triangle and visibly breaks his heart, marking a poignant end to the episode.

While the development of the love triangle between Jackie, Alex, and Cole initially flowed organically, this episode seems to force the romantic tension, potentially straining the natural progression of their relationships. Despite this, the show maintains its entertaining and enjoyable essence, keeping viewers engaged with the unfolding drama.