Jon Hamm’s Girlfriend Anna Osceola Should Look Familiar to ‘Mad Men’ Fans

Unlike many other celebrities, this Mad Men star has managed to keep his personal life private and stay out of tabloids for the wrong reasons. This has enabled the actor’s career to remain the central focus without being overshadowed by personal controversy. In fact, it took years for Jon Hamm’s relationship with his girlfriend, actor Anna Osceola to become red carpet official. Some people may not know who Osceola is, but she should look familiar to Mad Men fans.

Jon Hamm’s girlfriend Anna Osceola had a cameo in ‘Mad Men’

jon hamm girlfriend anna osceola
Jon Hamm and Anna Osceola attend the ‘Top Gun: Maverick’ world premiere on May 04, 2022 in San Diego, California. (Photo by Emma McIntyre/WireImage,)

Anna Osceola appeared in Mad Men’s series finale, playing a receptionist called Clementine who flirts with Jon Hamm’s Don Draper. The star and Hamm reportedly stayed in touch on and off, with rumors of their involvement swirling in May 2020. Before that, they had been spotted grabbing coffee in 2017, writes People. The pair hung out frequently in 2020, doing things like playing tennis and hanging out on the beach. Tabloids also reported that the two quarantined together.

Neither party confirmed nor denied the rumors. But it seemed as though the bachelor was off the market after he and Osceola were spotted enjoying exotic beach vacations together. In September 2021, the duo was pictured on a boat near Arco dell’Elefante in Pantelleria, Italy, spending quality time together.

Anna Osceola and Jon Hamm made their red carpet debut

After years of dating, Osceola and Hamm took their relationship to the next level. The couple made their red carpet debut at the Vanity Fair Oscars party in March 2022. The Vanity Fair party served as the first formal outing between the two after nearly two years of dating.

Hamm has never been married but was in a long-term relationship spanning nearly two decades with actor Jennifer Westfeldt. Hamm and Westfeldt began dating in 1997 and even worked together on a romantic comedy in 2011 titled Friends With Kids.

Hamma and Westfeldt called it quits in 2015. The Top Gun: Maverick star referred to his long-time love as “more than just a girlfriend,” despite never tying the knot officially. Their split was reportedly amicable, according to a statement.

“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,” it read. 

According to InStyle, the relationship may have ended due to Hamm’s substance issues and frequent partying. However, neither actors confirmed nor denied the speculation. Hamm was also linked to Ben Affleck’s ex Lindsay Shookus, in 2019.

Where you’ve seen Anna Osceola before

Unlike her significant other, Osceola hasn’t made much of a name for herself in showbiz. According to IMDb, she has 15 acting credits, dating back to 2007. The actor appeared in two Law & Order series: True Crime and Special Victims Unit. She also appeared in guest roles in shows like BullNCIS, and Rizzoli & Isles. 

Outside the procedural sphere, Osceola had a recurring role in the college dramedy Greek. The actor and her off-screen beau will reunite on screen in the upcoming film Confess, Fletch, alongside Mad Men favorite John Slattery. 

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