Things seem to be getting really serious between Jackie and Alex, with Jackie finally confessing her love to him at the end of the last episode. But does this mean she's completely over Cole now? In episode 9, it's officially spooky season, and Skylar decides to throw a Halloween party. Nothing could go wrong, or could it?
Spoilers are ahead from My Life with the Walter Boys season 2 episode 9.

Jackie and Alex struggle to go on a real date
Jackie and Alex are as happy as can be even though no one but Grace knows they're dating. Alex tells Jackie he wants to take her on a proper date, and they manage to plan a movie night. However, their plans are somewhat derailed when Skylar practically begs them to attend his Halloween party later that evening. Jackie and Alex then decide that they're going to attend Skylar's party first before dipping out to go on their date.
However, they're unable to go on the movie date once the time comes because Alex receives an urgent text from Kiley asking to meet. Their date is postponed once again. But it's not all bad. Jackie and Alex do finally get to go on a date. It's just not how they imagined. At the end of the ninth episode, Jackie invites Alex over to her Uncle Richard's house, and they spend intimate time together that way.
George's new business venture
George doesn't want to work on the guest ranch project anymore after realizing how stressful it is and how it keeps changing. Instead, he has a new business venture that he's hoping will fix his family's financial problems. In the last episode, George spoke to the owner of a local winery and shared his plan. Now we know what it is.
In the ninth episode, George and Katherine take Will to an unused part of their land. George then shares with Will that his great-grandfather used to grow grapes in that area and then used them to make wine. What he plans to do is start his own winery, but he needs to secure the money to get started first. So, he decides to lease the land to the local winery. This will give him immediate profit, which he can then use to pay back the investors. Although Will doesn't like his plan and would rather still go through with the guest ranch, he has no choice but to go along with it.
Later in the episode, George tells Richard about the plan. However, we never get to see if Richard is on board with the idea.
Cole and Dylan are back on bad terms
At the end of the previous episode, the Silver Falls High football team was required to take a drug test. Knowing that he had recently smoked a joint at the rodeo, Dylan asked Cole to take his test for him. However, we learn at the beginning of episode 9 that Cole chose not to go through with it, leaving Dylan to face the consequences on his own. Dylan ends up being suspended from the team, and Issac takes over his QB position in the meantime.
Later at Skylar's Halloween party, Cole tries to make amends with Dylan, but he ignores him. Through Dylan’s conversation with Kiley, we learn that his dad made a donation to the athletic department. By doing this, Dylan is still able to attend the showcase and will be put back on the football team soon. However, this turns Kiley off because she dislikes how his dad can simply throw money around and make his problems disappear. She finds it unfair.
Jackie breaks down at Skylar's party
Although it's Halloween, Jackie struggles with knowing that Día de los Muertos is the following day. Richard asks Jackie earlier in the episode if she wants to spend the holiday together before he has to leave for New York, but she doesn't give him an answer. According to Richard, Jackie didn't celebrate Día de los Muertos the year prior either. We find out the reason later.
It all has to do with what the holiday represents. It's about honoring and keeping alive the memory of deceased loved ones. After having a breakdown at Skylar's party, Jackie confides in Cole that the more she begins to fit in with the Silver Falls community, the more it feels like the memories of her late family members are slipping away. She doesn't want this to happen. That's why she failed her driver's test earlier that day. She's been struggling to process her grief.
As Jackie starts crying, Cole comforts and calms her down. Then, he takes her home. Now that she's in a much better headspace, Jackie texts Richard and tells him that she changed her mind. She meets with him at his house the next day to celebrate Día de los Muertos together before he leaves for New York. Jackie then texts Alex to come over. This is when they have their date.
Meanwhile, Cole finally receives his new SAT scores, and he does much better this time around. He wants to tell Jackie, so he heads to Richard's house. But once he arrives and opens the door, he catches Jackie and Alex making out on the couch. The ninth episode concludes here.
Here are three more important things that happen in the penultimate episode:
- Erin finds out about Jackie and Alex dating.
- Kiley and Alex finally patch up their friendship after Kiley calls him over to her house to help with her sick grandmother.
- Although we still don't know if Skylar rejected Zach, Zach keeps calling him.
My Life with the Walter Boys season 2 can now be streamed on Netflix.