Inside Jon Hamm's Relationship With Anna Osceola

Jon Hamm, who played the iconic Mad Men character Don Draper, somehow managed to make moodiness at work and smoking cigarettes look cool. There are few others who could pull off such skilled acting while working next to the talented powerhouses, January Jones and Elisabeth Moss. While Hamm is now a celebrated star, he has had his fair share of struggles, including a 2015 rehab stint. But since then, Hamm seems to be doing really well and we are cheering him on.

As for his love life, Hamm was in an 18-year-long relationship with actress Jennifer Westfeldt, but they called it quits in September 2015, according to People. The couple released a joint statement at the time of their breakup, saying (via Entertainment Tonight), "With great sadness, 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."

After the breakup, Hamm admitted to struggling in a 2017 interview with InStyle. He said, "It's hard. It's hard to be single after being together for a long time. It's really hard. It sucks." Luckily, it looks like life might not suck anymore for our favorite 1960s-era star, as Hamm has been photographed with a new leading lady. And she just so happens to have appeared in Mad Men as well!

Jon Hamm has been spotted hanging out with actress Anna Osceola in Los Angeles, and according to a June 2020 report from Us Weekly, they're dating. Osceola had a role in Mad Men playing the character Clementine, a young woman who greets Don Draper at the wellness center for the show's finale episode, "Person to Person," according to the Daily Mail. What's unusual to fans is that Mad Men ended in 2015, so it's surprising that Hamm and Osceola are only now beginning a relationship, but hey, these things take time.

Interestingly, according to Extra, Hamm and Osceola were first seen leaving a coffee shop together as far back as 2017. There were some quick sightings of the couple in 2018, but things are definitely gaining momentum lately, after picking back up in February 2020 when the couple was spotted getting breakfast, according to People. Since then, they've been seen playing tennis (like in the snapshot above) and enjoying each other's company. 

One possible reason for the lack of consistent sightings of Hamm and Osceola is because Hamm was briefly linked to Saturday Night Live TV producer Lindsay Shookus, according to a previous article by the Daily Mail. Those two were seen around New York City in late 2019. However, according to Page Six, they weren't actually dating. As for Hamm and Osceola's love story, fans rooting for the Mad Men pair will just have to stay tuned.