Wedding Bells? Jon Hamm's Inner Circle Convinced He's Gearing Up To Propose To GF Anna Osceola

Jon, who met Anna on the Mad Men set in 2015 — the same year he split from his partner of 18 years, actress Jennifer Westfeldt — said the past few years have left him crazing "being married, having kids, defining a new version of happiness, life, wellness."

“All that stuff that sounds hokey and whatever but it’s real and, for want of a better word, it’s what I’m working for. What else is there other than that," the actor told Stern.

Jon went on to explain that therapy and his successful love life have helped him heal the trauma of losing his mom at the age of 10 and unblock "a lot of ... availability and vulnerability."

When asked about his future with Anna, the star made it clear that he's happy in the direction they are going.

“It’s good and comfortable and it’s a feeling about taking care of someone else and being taken care of,” he stated.

Friends believe the next step is walking down the aisle, with a source spilling that "no one would be surprised if Jon pops the question before the year is out!"

Jon — who's 17 years older than Anna — made his red carpet debut with his much-younger lover in March, posing for photos at the Mercedes-Benz’s Academy Awards viewing party followed by Vanity Fair’s star-studded after-party.

However, the couple was spotted packing on the PDA way before they displayed their relationship to Hollywood's A-listers. Jon and Anna were photographed on a date in Santa Barbara, CA, in 2020, sparking dating rumors.

This is his first major romance since ending his relationship with Westfeldt in 2015. The duo, who started dating in 1997, announced their breakup in a joint statement, vowing to "continue to be supportive of each other in every way possible moving forward.”