A Timeline of Sylvester Stallone and Jennifer Flavin's 26-Year Marriage

May 2022 marked the couple's 25th wedding anniversary. Stallone celebrated the milestone with a heartfelt tribute to his wife on Instagram. "Happy 25th anniversary to my amazing wife," the actor captioned a slideshow of family photos from over the years. "There is not enough words to describe what this incredibly selfless dedicated, patient, woman has meant to our lives and I only wish they could be another 25! Thank you sweetheart!"