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Jon Hamm Is Still a Bachelor — Inside His Dating History Including Jennifer Westfeldt

Oyin Balogun
May 24, 2021
04:30 A.M.
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"Mad Men" star Jon Hamm has had an interesting love life over the years. From breaking up with his girlfriend of 18 years to romance rumors with some of Hollywood's finest actresses, here's a look into the actor's dating history so far.


At 50, "Mad Men" star Jon Hamm is still one of Hollywood's most eligible bachelors. But it has not always been this way. In the past, he has been linked to several beauties.

From Jennifer Westfeldt to Dakota Johnson to Anna Osceola, Hamm has been around—a lot! Want to know all about his dating history? Read on to find out!

Jon Hamm and Jennifer Westfeldt attend the Off-Broadway opening Night Performance of 'Billy & Ray' at the Vineyard Theatre on October 20, 2014 | Photo: Getty Images



Hamm met Westfeldt at a friend's birthday party in the late nineties and later reconnected when the actor helped Westfeldt run lines for an audition.

They started dating a year later, marking the beginning of what would turn out to be several years of love and bliss for the couple.

In the years that followed, Hamm and Westfeldt proved to be great support systems for each other both in their careers and personal lives.

Jon Hamm and actress Jennifer Westfeldt attend the 66th Annual Primetime Emmy Awards held at Nokia Theatre L.A. Live on August 25, 2014 | Photo: Getty Images


During Hamm's battle with alcohol addiction, Westfeldt was there to support the actor as he went through a 30-day treatment in a rehab facility. In their eighteen years together, Westfeldt and Hamm frequently talked about how they kept their love and relationship going.

The following month, it was no longer rumors as Us Weekly confirmed that Hamm and Osceola were dating.

In 2011, Hamm explained that he and Westfeldt go to great lengths to keep their lives how it was before they became famous. The actress also said they were like an old married couple.

Jon Hamm and Jennifer Westfeldt attend the Opening Night After Party for 'The Library' at The Public Theater on April 15, 2014 | Photo: Getty Images


It was, therefore, a shock to many when Hamm and Westfeldt announced their separation in 2015. A joint statement released by the couple revealed they would continue to be supportive of each other.

Though they were never married, Hamm and Westfeldt's breakup still stirred up several speculations as to why their relationship ended. A source close to the couple claimed that Westfeldt was tired of babying Hamm and had gotten tired of putting up with his party-hard lifestyle.

The actress reportedly wanted Hamm to grow up as she had seemingly grown tired of acting like a mother to him, and so, their relationship ended.


Jon Hamm (L) Jennifer Westfeldt arrive to the 2014 Vanity Fair Oscar Party on March 2, 2014 | Photo: Getty Images


Following Hamm and Westfeldt's breakup, many, including the media, developed an interest in the actor's life or, more specifically, his love life.


In June 2017, rumors started swirling that Hamm was dating his "Aardvark" co-star Jenny Slate after being photographed walking hand in hand.

However, the romance was not confirmed, and only a few months later, Hamm was rumored to be involved with "Fifty Shades" star Dakota Johnson.

Jon Hamm and Dakota Johnson during the 2019 Film Independent Spirit Awards on February 23, 2019 | Photo: Getty Images


They were spotted drinking wine together at New York's Kingside restaurant in the VIctory Central Park. A witness reported that the date lasted for about two hours as Hamm and Johnson appeared to have enjoyed each other's company.

Before the end of his romance with Westfeldt, Hamm was once rumored to have been dating his "Mad Men" co-star Elisabeth Moss, but it turned out to only be speculations.

But while Hamm continued to set the media abuzz, the actor also boasts of some grounded friendships such as the one he shares with January Jones.

Elisabeth Moss and Jon Hamm attend the Film Independent Special Screening of "Mad Men" at The Ace Hotel Theater on May 17, 2015 | Photo: Getty Images


Acting as a married couple in "Mad Men" for several years might have influenced Hamm's close-knit relationship with Jones, but nonetheless, fans love to see it.

In 2017, Hamm was once again in the news after sparking dating rumors with Ben Affleck's Lindsay Shookus after attending a Broadway show together.

Though there was no substance to the rumors, multiple sources noted that Hamm and Shookus sat next to each other and constantly flirted during the show.

Actor John Hamm at an interview on December 9, 2020 | Photo: Getty Images


That same year, Hamm was reported to have been seen leaving a coffee shop with his "Mad Men" co-star Anna Osceola. But it was not until three years later that they started sparking dating rumors.

In May 2020, Osceola and Hamm were pictured playing tennis together. A few days later, they were spotted together again, picking up food in Los Angeles.


The following month, it was no longer rumors as Us Weekly confirmed that Hamm and Osceola were dating. The couple also made no attempt to hide their romance.

In September 2020, Hamm and Osceola, who was clad in a green two-piece swimsuit, were spotted at a beach in Santa Barbara, enjoying the sun and giving fans a glimpse into their love.

With that, it became evident that Hamm had found love once again, and fans couldn't have been happier for the handsome actor and his new beau.