Jon Hamm surprised fans by tying the knot with his on-screen acquaintance turned real-life sweetheart, Anna Osceola.
The two were first introduced on the series finale of Mad Men back in 2015, the very year Hamm's 18-year-long relationship with actress Jennifer Westfeldt ended.
Over the course of his relationship with Jennifer, now 52, Jon was notably against marriage. He shared with Playboy in 2012 that his parents' divorce when he was just two years old shaped his perception of marriage.
"My parents got divorced when I was two and never remarried. So it doesn't mean anything to me," he shared.
"It's just my experience. I don't have that paragon of married life to look at and think, 'Oh yeah, that's it! That's what I want!'"
Similarly, Jon had no 'driving force' to become a parent, yet he never completely ruled out the possibility. Shortly after his encounter with Anna on the set of Mad Men, Jon and Jennifer announced their separation.
"We have decided to separate, after 18 years of love and shared history. We will continue to be supportive of each other in every way possible moving forward," they said in a joint statement to ET.
MORE: Jon Hamm makes rare statement about his future with girlfriend Anna Osceola
Rumors speculated that Jon's 'party-heavy lifestyle' was a bone of contention, with Jennifer yearning for him to 'grow up' and eventually tiring of 'being his mother.'
Fast-forward eight years, and Jon has exchanged vows with Anna, who is 17 years his junior.
Their relationship started blossoming in 2020, five years after they first met on the set of Mad Men, where Anna played a small role as a receptionist at a spiritual retreat attended by Hamm's character.
In a September 2022 appearance on Howard Stern, Jon, who once vowed he lacked the 'marriage chip,' hinted at a possible change of heart.
"This is all part of what I'm saying," he shared. "This is another place in my life that I feel very settled and comfortable. I'm in a relationship right now and it's comfortable."
He spoke of contemplating life's bigger picture, opening up possibilities like marriage, having children, and redefining happiness.
This shift in perspective also manifested in Jon’s engagement to Anna in February. A native of Cambridge, Massachusetts, Jon relocated to California to chase her Hollywood dreams. She's known for her roles in TV series such as Rizzoli & Isles, NCIS, and Law & Order.
The couple, who keep their private life away from social media, have been spotted together as far back as 2017.
Their travels around the globe and shared passion for tennis often place them in the public eye. They celebrated their love by saying 'I do' in a star-studded ceremony at Anderson Canyon in Big Sur, California - the very place they first met on Mad Men. The guest list boasted names like Paul Rudd, Tina Fey, and Brooke Shields.
Speaking with People, Jon mused over his journey to marriage. "It's a bumpy road towards relationships, but we do get better at it. I mean, I feel like I've figured out some things over the course of my half a century on the planet. So I'm in a pretty good place now."
He also touched on the complexities of two actors sharing life together. "You really have to lean on one another for their support and for any kind of advice."
Jon had been candid about seeking therapy to 'unpack' his childhood trauma, which he says has made his current relationship more meaningful.
Jon’s ex-partner Jennifer, 54, is reportedly single. During her time with Hamm, she expressed her uncertainties about having children.
"We don't [have children]. It's a tricky environment to bring them into. So not for us just yet," she told The New York Times in 2012. Despite acknowledging the possibility of regret, Westfeldt said, "I may wake up tomorrow with that lighting bolt, and I'll have to scramble to make it happen."