Jon Hamm Is Engaged to Anna Osceola — When Did They Start Dating?

It’s official! Mad Men alum Jon Hamm is getting hitched to actress Anna Osceola after two years of dating. Anna, who is 17 years his junior, previously appeared on Mad Men in its final season and also starred alongside Jon in the 2022 film Confess, Fletch. Let's take a closer look at their relationship timeline.

Jon and Anna are believed to have met in May 2015 when Anna guest-starred in Mad Men's series finale. Anna played the role of Clementine, a secretary at the retreat where Jon's character, Don Draper, ended up.

Just months later, Jon split from his girlfriend of 18 years, Jennifer Westfeldt. Their breakup came after Jon briefly went to rehab for an alcohol stint. An insider confirmed to ET that Jon's "party-heavy lifestyle" was the reason behind their breakup.

Two years later, Jon appeared to still be mourning the loss of their relationship. "It's hard. It's hard to be single after being together for a long time. It's really hard. It sucks," he told InStyle at the time.

However, Jon and Anna were also spotted hanging out for the first time in 2017, per People. They wouldn't be romantically linked until years later, though.

In 2020, Jon and Anna were spotted out together multiple times — including enjoying a beach day in Santa Barbara with one another — and it started to become obvious that they are more than friends.

The following year, they were also spotted vacationing in Italy.

In 2022, the pair made their first red carpet appearance at an Oscars viewing party in March. A few months later in September, Fletch, Confess (in which they both starred) came out.

In an interview on The Howard Stern Show that month, Jon talked highly of their relationship. "I'm in a relationship right now and it's comfortable," he told Howard, later adding that he's been able to sit down to start "really thinking about all that stuff, that's made the relationship that I'm in now even more meaningful and opened up the possibility of things like being married, having kids, defining a new version of happiness, life, wellness."

People reported in late February 2023 that Jon and Anna are getting hitched. No other details were provided about their big day, so fans will be on the lookout as more news unfolds.