Rob Kardashian has come a long way over the years — and Us Weekly is taking a look back at his journey! Born in March 1987 to Kris Jenner and the late Robert Kardashian Sr., the sole male Kardashian-Jenner sibling initially gained recognition through his family’s long-running reality series, Keeping Up With the Kardashians. He later used his celebrity status to land in second place on Dancing With the Stars’ 13th season in 2011. That following year, he launched a designer sock label called Arthur George. Rob eventually got his own KUWTK spinoff in 2016 titled Rob & Chyna, which he costarred on alongside his then-fiancée, Blac Chyna. The series only lasted for one season on E! Outside of entertainment, the reality star earned a college degree in 2009 from the University of Southern California’s Marshall School of Business. He also became a loving father to his daughter, Dream, whom he shares with Chyna. Despite his accomplishments, Rob has also faced some major hardships in the public eye. The California native has long struggled with his health, including being diagnosed with type 2 diabetes in 2015. The same year of his diagnosis, he was hospitalized for failing to take his insulin. He then said he was diabetes-free in 2016. Rob has also struggled with his weight over the years, leading him to avoid the spotlight and make infrequent appearances on his family’s TV show. The businessman, however, made major strides in recent years by committing to getting back in shape. In June 2020, he made headlines after debuting his dramatic weight loss at sister Khloé Kardashian’s 36th birthday party. Additionally, Rob faced legal trouble at the start of 2020 through a messy custody battle with Chyna. He filed a motion to obtain primary custody of the exes’ daughter. When the petition was denied, he filed another request with specific measures about visitation and custody of Dream. The former couple also made a series of allegations against each other, which they both subsequently denied. An insider told Us Weekly in August 2020 that Rob, who has also been linked to Adrienne Bailon and Rita Ora, had been “casually dating.” At the time, he was most recently associated with model Aileen Gisselle. Scroll down to check out photos of Rob through the years.