Ryan posted progression photos from Owen, 5, and his brother Troy's first day on Instagram.
Owen looked happy to begin his year as a kindergartener.
He later appeared absolutely miserable at the doctor's office. Ryan revealed he broke his arm after he fell of the monkey bars.
The injury was so bad that he now has to wear a cast. Owen, 5, was so distraught that he cried the rest of the day.
"First day of school was definitely one for the books!" Ryan captioned the set of pics along with funny hashtags like #atleasttheyrecute and #alwayssomething.
"Are you kidding me," RHOC star and family friend Tamra Judge wrote in the comments section. "This poor boy."
Briana gave birth to Owen on July 4, 2015. She and Ryan welcomed their other son Troy on September 28, 2012, months after getting married.