Cleveland Cavaliers player Tristan, 28 and Jordyn Woods, 22, hooked up at a party last February, marking the second time he had publicly cheated on the mother of his one-year-old daughter True.
'I feel like this whole situation needed to happen,' she told Khloé during the season 17 episode. 'For a reason ...for me, for her, for you, for everybody.'
'She was my security blanket,' Kylie said of Jordyn. 'She lived with me. We did everything together, and I feel like there's a part of me that needed to grow without her.'
'Sometimes people are there for certain reasons at certain times in your life, and then not there for others. Obviously, I love her. Right now, she's kind of doing her thing, I'm doing my thing.'
'I'm happy, for some weird reason,' Kylie concluded.
Khloé, who was still grappling with being cheated on, had planned the Napa trip as a way to figure out whether her sister wanted her to talk to Jordyn and repair their relationship.
'If this conversation didn't happen, I wouldn't know what a good headspace Kylie's in, so I feel good about that,' Khloé said afterward. 'And I am feeling better and better with every day.'
'I feel like this is the season to filter through the bulls***, and only the strong and loyal will survive,' she told Kylie.
As the episode opened, Khloé explained she'd recently had a therapy session with Tristan.
'I desire to have a good co-existing relationship with him, but I can't see myself ever being able to trust him,' she said, adding that Tristan felt the family turned their issues into a media circus.
'Not in a million years would you have wanted this public,' replied her sister, Kim Kardashian, 38.
Kim noted privately that she and her siblings often had to deal with unfounded rumors, noting that people usually wanted to believe the worst about them.
At one point in the show, she even called rapper French Montana to dispute rumors that Khloé, when she dated him, had stolen him away from his 'baby mama,' Trina, which he denied.
Khloé was trying to be sanguine about the more recent cheating scandal.
'At the end of the day, it's already out there, and if Tristan was going to cheat, he was going to cheat,' she conceded. 'It was going to be public at some point.'
She was just offended that Jordyn had done the cheating, she added.
The day before, Jordyn had texted her 'to talk,' and though she didn't want to, she wondered if she should do it for Kylie's sake.
'During all of this, the sad part is that Kylie lost her best friend, and I feel like sometimes my situation overshadowed hers,' Khloé explained in a confessional.
Later, as she shot a promo for Kylie's new skin-care line, she asked her sister to go to Napa with her, hoping they could have a 'heart to heart.'
At Del Dotto Vineyards, in Napa, they drank cabernet sauvignon from 'the world's first marble barrel,' with Kris, who said she'd like to be buried in it.
As she giggled away at another vineyard, Khloé broached the issue of Jordyn with Kylie.
'You lost a lifelong friend—I feel really bad about that,' Khloé said. 'I just want you to be happy.'
It wasn't the only difficult conversation to be had on the show.
Kourtney Kardashian, 40, and Scott Disick, 36, also got into it with Kris' partner, Corey Gamble, 38, after he suggested that their daughter Penelope, seven, needed a whipping.
The three oldest sisters had just joined their mom and Corey at a 'birthday party' for pal Jonathan Cheban, 45, who had officially changed his name to FoodGod.
Kourtney accidentally set off a heated discussion on discipline by announcing that Penelope had recently scratched her nanny, who quit on the spot.
'P can be out of control,' Kourtney said off-handedly. 'I think she almost blacks out, and does these wild things, but if you're a nanny… you could also say something to her, in the moment.'
Kris was concerned, saying: 'This is so much more serious than I think you realize. I had six kids. Not one time in my entire life did anyone ever have a complaint like this. Ever.'
'I scratched you, and I used to f***ing slap my nannies, like ''Bam!'' across the face,' Kourtney divulged.
She seemed unsure what to do next, as taking things away from Penelope hadn't worked.
'I'm sorry, but if P scratched me for no reason, I'm whipping her ass, and I'll explain it to y'all later,' Corey interrupted. 'I would give her a spanking for sure.'
Scott was instantly in a fury, yelling: 'You would whip my daughter's ass if she scratched you? A little [seven]-year-old girl? What the f*** are you talking about?'
'You are not going to beat my little daughter. Get the f*** out of here!' he raged. 'Don't ever talk about a child like that! Ever. Ever. Anyone's child!'
'Whipping is a discipline, motherf***er, what you talking about?' Corey rejoined. 'I'll whip your ass!'
'If your kids scratched me in the face, you don't think they deserve to be popped?' he asked both parents.
'Not at all,' Kourtney said flatly, as she and Scott underscored the harm in it.
'That's how anybody talks about disciplining their kids—whip their ass,' Corey replied.
Kourtney announced then that Corey would never be alone with her kids, telling Kris that if he was, 'there will be a f***ing issue.'
Kris began crying as everyone left the restaurant.
Corey later made up with Kourtney, saying he had been speaking generally, and did not want to discipline her kids.
'In my culture, whipping your kids—that's just normal,' he said in a confessional. 'It's important that you understand consequences.'
'But I don't have kids, so obviously I'm not going to be disciplining no kids,' Corey added.
Kourtney struggled with her children's behavior throughout the episode.
In one visit to her sister's house, Khloé watched appalled as all three of Kourtney's kids—Mason, nine; Penelope; and Reign, four, casually hit their mother and made demands.
'Give me cough drops!' Reign growled at her, as Khloé's eyes widened.
When Kourtney took too long to respond, he demanded: 'Go, mom!' and swiped at her.
Kourtney wanted to be strict, but tried to keep things positive, she said.
'Growing up, my dad was more strict than my mom, but he would do it in a loving way,' she recalled. 'And so I try to be more like that, but I'm not the best at it.'
She later got a call from the principal at Mason's school, who told her that Mason had just been spoiling for a fight with a classmate during a handball game.
Each of the boys had wanted to serve the ball, and Mason asked him, 'Do you wanna fight?'
The principal noted that Mason would be writing an apology letter to that child the following Monday, and Kourtney wondered if she should ground him that weekend.
She decided not to, saying: 'I just think it's normal kid stuff.'
'People makes mistakes, babe, and then they have consequences, like, you're gonna go in and write the letter and apologize,' she told Mason. 'You're learning and growing.'
Kid stuff: Kourtney after Mason got in trouble at school decided against grounding him
She went with Khloé to a cryotherapy session, where temps dipped to minus 213F.
On the way home, they called Scott to tell him about his son's infraction.
He was naturally upset, calling it 'very serious.'
'He asked the kid if he wanted to fight him!' Scott said. 'No chance he should be at a sleepover!'
In a confessional, Scott said that he'd had a lot of problems with authority when he was a kid, and hadn't faced many consequences, but that he didn't want his kids to grow up the same way.
Later, he decided it was best that he and Kourtney just handle those issues themselves.
'Having such a big family, we thought we would have a lot of people to lean on and get advice from, but I definitely think our children's behavior should be dealt with between Kourtney and I,' he decided.
The family was equally frustrated about another matter involving Kim's security measures.
Kim had tightened her security in the wake of area robberies, still feeling vulnerable after her own 2016 attack in Paris, during which she was robbed of $10 million in jewels.
'It's going to seem a little bit excessive for a minute, but it's what makes me feel safe,' she said.
Kris complained that just popping over to see Kim had become a military operation.
Tough security: Kris Jenner complained about the tough new security at Kim's house
'Every time I go over there, they still don't know who I am,' she told Khloé, explaining that she was repeatedly asked to show ID.
'She has, like, a Navy SEAL team over there,' Kris noted. 'I want her to be safe…we should be able to come and go at least a little more freely, that's all.'
Khloé pointed out that Kris had always stressed the importance of good security.
'One hundred percent,' Kris emphasized. '[But] I think her family should have clearance. I go over there and it's thumbprints and signatures, and, I mean, what's your blood type?'
'We have all the clearance in the world,' Khloé retorted. 'You just have to go through the front door. You don't hop a fence to go to the back yard.'
Kourtney later spoke with Kim about it while she underwent Emsculpting, a high-intensity electromagnetic procedure aimed at sculpting her abs.
The eldest sibling told Kim that she and Scott had been asked for their names on a recent visit and 'they almost asked me to sign an NDA.'
Jonathan also had a problem with it when he showed up.
'I don't do administrative work like this,' he told security.
As Kim rode home from an appointment one day, she got an urgent call from Khloé.
'Oh my god, Kim you've got to come—your whole security just tackled mom,' she cried. 'We just called 911. This is so crazy.'
'Oh my god—why would someone tackle my mother?' Kim said, watching surveillance video.
She spotted her mom on a stretcher outside her home and ran to her.
'I can't move my neck,' moaned Kris, wearing a collar, as Kim freaked out.
'Mom—say it!' Khloé begged her.
Surveillance video: Surveillance video shockingly showed Kris being tackled
'Got you,' Kris said.
The momager was proud of herself for pulling off 'the prank of the century,' even hiring a body double and fake security officers.
'You cannot joke like that. This is not funny,' Kim stressed.
'This was too dark for my soul,' Khloé agreed.
The prank seemed to work as Kim said she would make changes to her security procedures.
Keeping Up With The Kardashians will return next week on the E! network.
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