Rob became a father in November 2016 when his then-girlfriend, Blac Chyna, gave birth to their daughter. The pair, who went public with their romance earlier that year, dated off and on until their 2017 split.
Following their breakup, Rob and Chyna made headlines for multiple legal battles while attempting to coparent their child. In April 2022, Rob took the stand in a trial for Chyna’s defamation lawsuit against Kris Jenner, Kim Kardashian, Khloé and Kylie Jenner.
A judge ultimately ruled in the Kardashian-Jenner family’s favor and Chyna was not awarded any damages after originally seeking more than $100 million. Khloé, for her part, later waved off notions that the lawsuit affected her bond with Dream.
“Rob does such an incredible job with [Dream] and I’m just there to help whenever he needs. I do not have a relationship with Dream’s mom,” the Good American cofounder said in a July 2023 episode of The Kardashians. “It is hard to have a relationship with someone when they sue you for hundreds of millions of dollars.”
Disick, meanwhile, showed support for Khloé and her dedication to her loved ones. “You’re, like, the wheel that makes the car move,” he noted.
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Scroll down for Khloé and Dream’s sweetest moments over the years: