Disick has more experience than perhaps anyone with being the controversial boyfriend of a Kardashian. Since he and Kourtney split up for good, he seems to be on better terms than ever with her family. The show is currently revealing events from back in the spring, when Thompson was caught cheating on Khloe Kardashian, and her family was furious.
The latest sneak peek shows Disick visiting Kardashian in her home gym in Calabasas, California. He comes in with good humor, joking with Kardashian about the amount of equipment she has while she scrolls on her phone, not laughing along. Finally, Disick sits a chest press machine and screams as he tries to move the weight, drawing her attention.
"I feel like Khloé is living a full double life," Kardashian says, finally looking at Disick. "She's in town and I just haven't seen her. I feel like Tristan is here and she's so nervous for him and I to see each other. I feel like I get into this protection mode where I just like, go into worst case scenario."
Khloe was alone in Cleveland, Ohio when Thompson was caught on camera with another woman. Thompson was in New York City for a game. Khloe gave birth two days later, and she returned home to see her family after six weeks, as soon as True was cleared to fly.
"I think sometimes, when people get too caught up when it's a negative protection and not always being there for the positive, then everybody feels kind of like, attacked," Disick says.
"Is it annoying when family members start ganging up on you?" Kardashian asks, apparently looking for a more direct answer.
"Listen, no matter what you say to somebody when there's something happening in their life, it's not actually going to be taken in," Disick says. "I know back in the day when your mom or Khloé would get involved in me and Kourtney's stuff, it only would draw us farther away from the family."
Disick and Kourtney had years' worth of drama in their day, including Disick's own trouble with alcohol.
"It never pulled anybody in and made people more comforted," he remembers. "And now, look — you're being protective because you love your sister, but guess what? Now your sister is in Calabasas, flew home, and doesn't want to see you. So it's like, what did you solve?"
To see how Kardashian utilizes Disick's advice, fans will just have to tune in this week. Keeping Up with the Kardashians airs on Sundays at 9 p.m. ET on E!