John started dating Ali when he was 19 and she was 17. When they got engaged in December 2017, his sisters were present and even went dress shopping with Ali in November 2018.
“I said yes to my dress!! This was the most amazing experience with 4/6 of my bridesmaids, my mom, and future mother in law💖💖,” she wrote via Instagram at the time. “I am so thankful that everyone came to NYC for this! And special thank you to @bridalreflectionsny & @galialahav for making my dress dreams come true👰🏼 #allthetears.”
While Sydney threw Ali a baby shower in November 2019, Jessie did not appear to be in attendance. Months earlier, Ali shared a photo with Jessie and John at the singer’s “best show” in April 2019.
They welcomed daughter Emmy in December 2019 and daughter Callie in June 2021.
In July 2022, Jessie attended John and Ali’s wedding. He confirmed via photos shared on Instagram that both of his sisters were there.
“So incredibly grateful for yesterday. It truly felt like the highlight of my life to share that moment with my friends and family. After 4 years of trying, I finally got to marry my best friend @aligreen13,” John wrote.See Full Gallery