Things were intense when Kourtney Kardashian and Scott Disick started dating. They even planned to go to Las Vegas and have a shotgun wedding (per Cheat Sheet), but Kourtney’s family talked her out of the sudden wedding plans. In the first season of the 2011 “KUWTK” spinoff “Kourtney and Kim Take New York,” Scott hoped to propose to Kourtney over dinner, but decided otherwise after a conversation with her. “Why mess it up?” Kourtney asked him (per Us Weekly). “I just feel like right now I’m happy with the way things are.” There was little progress after that.
Socialite Scott’s life involved much partying, and according to Cheat Sheet, Kourtney could not entertain the idea of marrying him until he could figure out his priorities. “She’s made comments to her family about how his behavior [with money and partying] is exactly why she never married him,” an insider claimed (per Cheat Sheet). “He doesn’t really have a job beyond his club appearances and paid Instagram posts and hasn’t given up drinking.”
But things did get better. In October 2017, Kourtney took to Instagramto post a picture of herself and her former flame enjoying the great outdoors on what appeared to be a hike. “MOM and DAD back at it again with the co parenting skills,” the Poosh founder wrote.