Mad Men’s Jon Hamm finds love with Anna Osceola as he pops the question!

Jon Hamm’s Engagement To ‘Mad Men’ Co-Star


Hollywood actor Jon Hamm, popular for his role as Don Draper in hit AMC drama “Mad Men” has proposed to Anna Osceola after two years of dating according to People Magazine.

The Beginning:

Jon Hamm and Anna Osceola first met on the set of the “Mad Men” series finale in 2015. Hamm starred as Don Draper while Anna starred as Clementine, the receptionist at the spiritual retreat that Don Draper attended. Hamm and Anna, however, were not romantically linked until 2020 when they started dating.

The Relationship:

The loved-up couple started dating each other in 2020. Jon Hamm was previously in a long-term relationship with actress and screenwriter Jennifer Westfeldt from 1997 until they split in 2015.

The Proposal:

The couple got engaged in 2022 after dating for two years. According to reports, the actor is “very much” in love with Anna Osceola and their relationship is “meaningful”. Hamm recently revealed he is open to the possibility of getting married and having kids.

The Red Carpet Debut:

The couple made their red carpet debut last year at an Oscars afterparty. They also reunited on-screen in the third installment of the Fletch franchise, Confess, Fletch in which Jon took on the role of Irwin M. Fletcher and Anna played Larry.

Hamm’s Comments:

According to an interview Jon gave on Howard Stern’s SiriusXM show, the actor shared that he was at a “comfortable” stage in his life where he could envision himself getting married. Hamm also added 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.

The Engagement:

Reps for Hamm and Osceola, however, have not commented on the reported engagement, and fans of the actors will have to wait for an official announcement to get confirmation of the news.

The Couple’s Privacy:

Both Jon Hamm and Anna Osceola keep off social media and have lived a very private life until their relationship heated up and went public.


The news of Jon’s engagement to his Mad Men’s co-star has been making headlines as of late, and while there is still no official word on it from either party, the fans of both actors are excited to see what the future has in store for them.


Q1. Who is Jon Hamm and what is he famous for?

Jon Hamm is an American actor famous for his role as Don Draper in the hit AMC drama series “Mad Men”.

Q2. Who is Anna Osceola?

Anna Osceola is also an American actress who starred alongside Jon Hamm in Mad Men.

Q3. When did Jon Hamm and Anna Osceola first meet?

Jon Hamm and Anna Osceola first met on the set of the “Mad Men” series finale in 2015.

Q4. When did Jon Hamm propose to Anna Osceola?

Jon Hamm proposed to Anna Osceola in 2022 after the pair had been dating for two years.

Q5. What is the reaction to the news of Jon Hamm’s engagement with Anna Osceola?

Fans of both actors are excited to see what the future has in store for them despite there being no official confirmation.