Now, the reality star battles a new challenge: Raising his baby as a single dad.
Rob posted on Instagram Tuesday a selfie of him and Dream, writing, "Saying bye to my beautiful baby girl ..... she is smiling at me. U see how she looking at her daddy. I literally can't get enough of this girl,,, I never felt a love or happiness like this ever in my life and she makes me so happy ,,,about to miss her so much. Love You baby Dream."
Rob shares Dream with Blac Chyna, who began dating him just over a year ago. Last month, a source close to Rob told E! News that the they are not together and are living in separate homes.
The source added that Rob is focusing more "on himself, the baby and work," particularly his Arthur George sock line.
His and Chyna's breakup came months after a more public, drama-filled brief split in December and following a fight earlier last year. Rob and Chyna, who got engaged months after they started dating, aired some of their dirty laundry on Keeping Up With the Kardashians and their spinoff Rob & Chyna.
Rob had returned to Keeping Up With the Kardashians in 2015 after an almost two-year hiatus, during which he largely staying out of the public eye and social media as he battled weight gain and other personal issues. His turmoil was documented on the show. That December, Rob was hospitalized briefly and diagnosed with diabetes.
After he and Chyna took their relationship public in January 2016, he was spotted out in public more, posted more on social media and appeared happier and more fit. She was credited with helping him become healthier, cooking him meals and taking him to the gym.
But amid his turmoil with Chyna, Rob continued battling personal, health and weight issues, as documented on Rob & Chyna.
Just after their previous breakup in December, Rob wrote that he was an "emotional bad place" and was seeking help to deal with his "flaws" and "issues." The following week, and a year after his original diabetes scare, he was hospitalized again briefly after suffering complications from the disease.
In January, Rob and Chyna appeared to be on the road to reconciliation, appearing together at a strip nightclub in New York City and celebrating the one-year anniversary of the day they started going out. But they spent Valentine's apart and Blac Chyna stopped wearing her engagement ring, sparking breakup rumors that E! News later confirmed.
The drama may be continuing to take its toll on Rob's health, but with the opposite effect; some commentators noted that in his latest photo with Dream, his face looks thinner than usual.
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Kim Kardashian & Blac Chyna's Friendship Before Rob Kardashian Romance
But Rob is slowly moving on and appears determined to make 2017 the best year yet, for him and his baby girl as he continues to bond with her and co-parent her with his now-ex.
His first post this year was a photo of him holding Dream. He also shared a picture of him kissing her as she lies on an examining table at the pediatrician's office during her two-month check-up.
"Dreamy Dream bean got her first shot today and she is 2 months old ! Woohoooooo," Rob wrote. "I wanted a boy so bad and now that I got my girl I am so Thankful and Happy for her and wouldn't want it any other way ! She is the best and I love her so much and I thank God every day for her cuz she is the best and she is my best friend :) LOL I love her so much ‼️"
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Kris Jenner, Rob Kardashian, Dream KardashianSnapchat
And Rob isn't alone; his family has been supporting him through and through and is, as expected, enamored with Dream. Rob has often brought the baby to see her grandma Kris Jenner and the rest of his family. His sisters have occasionally posted pics and videos of themselves holding the child.
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