Jon Hamm Is Dating His Former “Mad Men” Costar Anna Osceola

June 24, 2020 / Posted by:

Hey, look over here! Did you hear? Jon Hamm has a new girlfriend and you are definitely not getting official confirmation of this exciting new development from Us Weekly today because everybody saw Jon’s sooted up face beaming out from underneath a Buckwheat wig yesterday. No! Don’t go looking for it right now, stay with me, the sexy news is RIGHT HERE!

According to Us Weekly, you never even saw that Jon was in two of four 30 Rock sketches featuring blackface that Tina Fey and Robert Carlock asked to be removed from streaming services. But just in case you did, please remember that this very handsome man used to be single, but is now dating actress Anna Osceola, who appeared on the final season of Mad Men.

Off the market! Jon Hamm and actress Anna Osceola are dating, Us Weekly confirms.

The Mad Men alum, 49, sparked romance rumors with Osceola, 32, earlier this year after being spotted together on multiple occasions amid the coronavirus pandemic.

Anna played the hippy receptionist at the Esalen-like retreat where Jon’s character Don Draper has his breakdown and subsequent Coca-Cola epiphany. Us Weekly notes that they’ve been spotted around LA doing couple-y things, like getting takeout, and that fans have been speculating about their relationship since May. But John and Anna have been hanging out since 2017, so the sudden interest in their relationship is highly suspect.

The two wore cloth masks over their mouths and noses as they walked from their car to the court in Los Angeles, in photos published by the Daily Mail on May 22. Hamm wore a hat and green shorts while Osceola donned a white and green tennis dress and visor.

The lovebirds were previously spotted together in 2018 playing tennis, according to the Daily Mail, and Extra reported that in 2017 they were seen leaving a coffee shop.

I guess Lindsay Shookus never had a chance. Here are Jon and Anna on the court.

Are those tennis balls in his pocket or gerbils for his snake? Here are Jon and Anna out together in May. I apologize in advance for deflating any anticipatory groin-area engorgement with these photos. The Hammaconda is hibernating and Jon looks like he got woken up by a fire alarm in the middle of the night and had to get dressed in a hurry with no idea what the weather might be like.

Honestly, I’m more mad at those shorts than I am about Jon’s half-assed blackface. Here they are yet again, this time back in February of last year. Jon looks like he just saw a ghost wearing “race-changing” makeup in that last one.

Judging by this “breaking news,” I’m going to go out on a limb and say we can add afro-wigs and overalls to the growing list of subjects Jon doesn’t want to talk about.


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